HCID 59472011, compound → 3-[5-[3-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

HRID 2204858Notes

Reaction equation

HRID 2204858 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH:31]([CH3:35])[CH2:32]CO)(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10](C2C=CC(CNC)=CC=2)=[N:11][N:12]=1.[NH2:36][CH2:37][C:38]1[CH:39]=[C:40](C2OC(C3C(N)=NC=C(C4C=CC=CC=4S(C)=O)N=3)=NN=2)[CH:41]=[CH:42][CH:43]=1.FC1C=C(C2N=C(C3OC(C4C=CC(CNC)=CC=4F)=NN=3)C(N)=NC=2)C=CC=1S(C(C)C)(=O)=O.ClC1C=C(C2N=C(C3OC(C4C=CC(CNC)=CC=4F)=NN=3)C(N)=NC=2)C=CC=1S(C(C)C)(=O)=O.NC1N=CC(C2C=CC(S(C(C)CCO)(=O)=O)=CC=2)=NC=1C1OC(C2C=CC(CNC)=CC=2F)=NN=1>>[NH2:36][CH2:37][C:38]1[CH:43]=[C:42]([C:10]2[O:9][C:8]([C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:22]4[CH:23]=[CH:24][C:25]([S:28]([CH:31]([CH3:32])[CH3:35])(=[O:30])=[O:29])=[CH:26][CH:27]=4)[N:6]=3)=[N:12][N:11]=2)[CH:41]=[CH:40][CH:39]=1

Participants

6

Reactant 5

HCID 59472011HCID 59472011, compoundHCID 59472380HCID 59472380, compoundHCID 70842371HCID 70842371, compoundHCID 90435574HCID 90435574, compoundHCID 90435594HCID 90435594, compound

Product 1

HCID 594716333-[5-[3-(Aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

Procedure

Compound IA-88 3-[4-[5-amino-6-[5-[4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]phenyl]sulfonylbutan-1-ol 1H NMR (400 MHz, DMSO) d 1.21 (d, 3H), 1.38-1.47 (m, 1H), 1.97-2.05 (m, 1H), 2.64 (t, 3H), 3.38-3.46 (m, 2H), 3.51-3.56 (m, 1H), 4.29 (t, 2H), 7.77 (d, 2H), 7.97-8.01 (m, 2H), 8.26 (d, 2H), 8.40-8.44 (m, 2H), 8.97 (s, 2H) and 9.09 (d, 1H) ppm; MS (ES+) 495.0 Compound IA-257 3-[5-[3-(aminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]-5-(2-methylsulfinylphenyl)pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 3.1 (s, 3H), 4.3 (s, 2H), 7.6-7.75 (m, 4H), 8.05 (d, 1H), 8.15 (d, 1H), 8.35-8.5 (m, 4H) and 8.9 (s, 1H) ppm; MS (ES+) 407.1 Compound IA-321 5-(3-fluoro-4-isopropylsulfonyl-phenyl)-3-[5-[2-fluoro-4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 1.25 (d, 6H), 2.7 (s, 3H), 3.5-3.6 (m, 1H), 4.4 (s, 2H), 7.6 (d, 1H), 7.7 (d, 1H), 7.9 (t, 1H), 8.2-8.3 (m, 2H), 8.35 (t, 1H), 8.9-9.0 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 501.3 Compound IA-329 5-(3-chloro-4-isopropylsulfonyl-phenyl)-3-[5-[2-fluoro-4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-amine 1H NMR (400 MHz, DMSO) d 1.25 (d, 6H), 2.7 (s, 3H), 3.7-3.8 (m, 1H), 4.4 (s, 2H), 7.6 (d, 1H), 7.7 (d, 1H), 8.1 (d, 1H), 8.25-8.35 (m, 2H), 8.4 (s, 1H), 8.9-9.0 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 517.2 Compound IA-342 3-[4-[5-amino-6-[5-[2-fluoro-4-(methylaminomethyl)phenyl]-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]phenyl]sulfonylbutan-1-ol 1H NMR (400 MHz, DMSO) d 1.25 (d, 3H), 1.4-1.5 (m, 1H), 1.95-2.03 (m, 1H), 2.7 (s, 3H), 3.4-3.5 (m, 1H), 3.5-3.6 (m, 1H), 4.45 (s, 2H), 4.6-4.7 (m, 1H), 7.6 (d, 1H), 7.7 (d, 1H), 8.0 (d, 2H), 8.3 (t, 1H), 8.4 (d, 2H), 9.0 (br s, 2H) and 9.1 (s, 1H) ppm; MS (ES+) 513.2

Sources & evidence

ORD record
ord-fda5adb1ac6a42ada2fd864b1f1b9135
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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