HCID 59471789, compound → HCID 59472090, compound

HRID 2204896Notes

Reaction equation

HRID 2204896 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH:29]([CH3:33])[CH2:30][CH2:31][OH:32])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[N:6][C:7]=1[C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:11][N:12]=1.[CH3:34]N(C)CCC(S(C1C=CC(C2N=C(C3OC(C4C=CC=CC=4F)=NN=3)C(N)=NC=2)=CC=1)(=O)=O)C.FC1C=CC=CC=1C1OC(C2C(N)=NC=C(C3C=CC(S(C4CCOC4)(=O)=O)=CC=3)N=2)=NN=1>>[F:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[O:9][C:8]([C:7]2[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH:29]4[CH2:33][CH2:34][O:32][CH2:31][CH2:30]4)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[N:6]=2)=[N:12][N:11]=1

Participants

4

Reactant 3

HCID 59471789HCID 59471789, compoundHCID 59472031HCID 59472031, compoundHCID 59472280HCID 59472280, compound

Product 1

HCID 59472090HCID 59472090, compound

Procedure

Compound IA-339 3-[4-[5-amino-6-[5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-yl]phenyl]sulfonylbutan-1-ol 1H NMR (400.0 MHz, DMSO) d 1.20 (d, 3H), 1.37-1.46 (m, 1H), 1.99-2.02 (m, 1H), 3.38-3.43 (m, 2H), 3.52 (s, 1H), 4.66 (t, 1H), 7.50-7.59 (m, 2H), 7.77 (d, 1H), 7.97 (d, 2H), 8.20 (s, 1H), 8.37 (d, 2H) and 9.08 (s, 1H) ppm; MS (ES+) 470 Compound IA-343 5-[4-[3-(dimethylamino)-1-methyl-propyl]sulfonylphenyl]-3-[5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl]pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 1.20 (d, 3H), 1.76-1.82 (m, 1H), 2.14-2.20 (m, 1H), 2.79 (s, 6H), 3.21 (s, 2H), 3.47-3.55 (m, 1H), 7.50-7.59 (m, 2H), 7.75-7.81 (m, 1H), 8.01 (d, 2H), 8.19 (m, 1H), 8.40 (d, 2H), 9.10 (s, 1H) and 9.58 (s, 1H) ppm; MS (ES+) 497 Compound IA-349 3-[5-(2-fluorophenyl)-1,3,4-oxadiazol-2-yl]-5-(4-tetrahydrofuran-3-ylsulfonylphenyl)pyrazin-2-amine 1H NMR (400.0 MHz, DMSO) d 2.13-2.19 (m, 2H), 3.65 (m, 1H), 3.74-3.80 (m, 1H), 3.86 (dd, 1H), 4.04 (dd, 1H), 4.22-4.28 (m, 1H), 7.50-7.60 (m, 2H), 7.75-7.80 (m, 1H), 8.04 (d, 2H), 8.20 (m, 1H), 8.38 (d, 2H) and 9.09 (s, 1H) ppm; MS (ES+) 468

Sources & evidence

ORD record
ord-5635df21159745bd809001676b799461
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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