4-[5-Amino-6-[5-(2-methoxyanilino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamide → 4-(5-amino-6-(5-(benzylamino)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamide

HRID 2204815Notes

Reaction equation

HRID 2204815 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:22]2[CH:32]=[CH:31][C:25]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:24][CH:23]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([NH:13]C2C=CC=CC=2OC)=[N:11][N:12]=1.NC1N=CC(C2C=CC(C(N(C)C)=O)=CC=2)=NC=1C1OC(N[C@H:46]([C:48]2[CH:53]=[CH:52][C:51](Cl)=[CH:50][CH:49]=2)C)=NN=1.NC1N=CC(C2C=CC(C(N(C)C)=O)=CC=2)=NC=1C1OC(NCCC2C=CC=CC=2)=NN=1.NC1N=CC(C2C=CC(C(N(C)C)=O)=CC=2)=NC=1C1OC(NC2CCCCC2)=NN=1.NC1N=CC(C2C=CC(C(N(C)C)=O)=CC=2)=NC=1C1OC(NC2C=CC=C(C#N)C=2)=NN=1.C(NC1OC(C2N=C(C3C=CC(C(N(C)C)=O)=CC=3)C=NC=2N)=NN=1)(=O)C.NC1N=CC(C2C=CC(C(N(C)C)=O)=CC=2)=NC=1C1OC(NC(=O)C2C=CC=CC=2)=NN=1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:22]2[CH:23]=[CH:24][C:25]([C:26]([N:28]([CH3:30])[CH3:29])=[O:27])=[CH:31][CH:32]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([NH:13][CH2:46][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[N:11][N:12]=1

Participants

8

Reactant 7

HCID 594716144-[5-Amino-6-[5-(2-methoxyanilino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594716444-[5-Amino-6-[5-(3-cyanoanilino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594717044-[5-Amino-6-(5-benzamido-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594717714-[6-(5-Acetamido-1,3,4-oxadiazol-2-yl)-5-amino-pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594720324-[5-amino-6-[5-[[(1S)-1-(4-chlorophenyl)ethyl]amino]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594722464-[5-Amino-6-[5-(cyclohexylamino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamideHCID 594722644-[5-Amino-6-[5-(phenethylamino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-n,n-dimethyl-benzamide

Product 1

HCID 594717924-(5-amino-6-(5-(benzylamino)-1,3,4-oxadiazol-2-yl)pyrazin-2-yl)-N,N-dimethylbenzamide

Procedure

Compound IA-103 4-[5-amino-6-[5-(2-methoxyanilino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 3.03 (s, 3H), 3.07 (s, 3H), 3.94 (s, 3H), 7.07-7.10 (m, 1H), 7.15-7.17 (m, 2H), 7.59 (d, 2H), 7.75 (br s, 2H), 8.12-8.19 (m, 3H), 8.94 (s, 1H) and 10.17 (s, 1H) ppm; MS (ES+) 432.16 Compound IA-129 4-[5-amino-6-[5-[[(1S)-1-(4-chlorophenyl)ethyl]amino]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 1.50 (d, 3H), 2.96 (s, 3H), 3.01 (s, 3H), 4.83 (d, 1H), 7.40-7.47 (m, 4H), 7.51-7.54 (m, 4H), 8.06 (d, 2H), 8.81 (s, 1H) and 8.90 (br s, 1H) ppm; MS (ES+) 464.16 Compound IA-156 4-[5-amino-6-[5-(phenethylamino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 2.77 (s, 1H), 2.94 (t, 4H), 3.00 (s, 3H), 3.04 (s, 1H), 3.51-3.56 (m, 2H), 7.22-7.24 (m, 1H), 7.28-7.34 (m, 4H), 7.52 (d, 2H), 7.61 (s, 1H), 8.05-8.07 (m, 2H), 8.32 (t, 1H) and 8.81 (s, 1H) ppm; MS (ES+) 430.2 Compound IA-163 4-[5-amino-6-[5-(cyclohexylamino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 1.17-1.19 (m, 1H), 1.30-1.35 (m, 4H), 1.57-1.60 (m, 1H), 1.74-1.76 (m, 2H), 1.99 (s, 2H), 2.96 (s, 3H), 3.00 (s, 3H), 3.48 (br s, 1H), 7.52 (d, 2H), 7.62 (br s, 2H), 8.06 (d, 2H), 8.20 (d, 1H) and 8.81 (s, 1H) ppm; MS (ES+) 408.22 Compound IA-254 4-[5-amino-6-[5-(3-cyanoanilino)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 2.97 (s, 3H), 3.01 (s, 3H), 7.54 (t, 3H), 7.63 (t, 1H), 7.75 (br s, 1H), 7.91 (dd, 2H), 8.09-8.13 (m, 3H), 8.91 (s, 1H) and 11.51 (s, 1H) ppm; MS (ES+) 427.15 Compound IA-278 4-[6-(5-acetamido-1,3,4-oxadiazol-2-yl)-5-amino-pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 2.20 (s, 3H), 2.96 (s, 3H), 3.01 (s, 3H), 7.54 (d, 2H), 7.66 (br s, 2H), 8.08 (d, 2H), 8.92 (s, 1H) and 11.92 (s, 1H) ppm; MS (ES+) 368.13 Compound IA-287 4-[5-amino-6-(5-benzamido-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N,N-dimethyl-benzamide 1H NMR (400.0 MHz, DMSO) d 2.96 (s, 3H), 3.00 (s, 3H), 3.31 (s, 1H), 7.52-7.61 (m, 4H), 7.69 (t, 2H), 8.06-8.12 (m, 4H), 8.95 (s, 1H) and 12.35 (br s, 1H) ppm; MS (ES+) 430.14

Sources & evidence

ORD record
ord-643e17e316ea4201a5fce2117c71dd5c
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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