HCID 59471861, compound → HCID 59471918, compound

HRID 2204877Notes

Reaction equation

[NH2:1][C:2]1[C:3]([C:20]2[O:24][C:23]([NH:25][C:26]([C@@H:28]3[C@H:33]4C[C@H:30]([CH2:31][CH2:32]4)[NH:29]3)=[O:27])=[N:22][N:21]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:6][N:7]=1.NC1C(C2OC(NC([C@@H]3CCCN3)=O)=NN=2)=NC(C2C=CC(S(C(C)C)(=O)=O)=CC=2)=CN=1>>[NH2:1][C:2]1[C:3]([C:20]2[O:24][C:23]([NH:25][C:26]([C@@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)=[O:27])=[N:22][N:21]=2)=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:18])[CH3:19])(=[O:15])=[O:16])=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

Reactant 2

HCID 59471861HCID 59471861, compound

HCID 90435588HCID 90435588, compound

Product 1

HCID 59471918HCID 59471918, compound

Procedure

Compound IA-160 (1R,4S,6S)—N-[5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]-5-azabicyclo[2.2.1]heptane-6-carboxamide 1H NMR (400.0 MHz, DMSO) d 1.18 (d, 6H), 1.34-1.45 (m, 2H), 1.55-1.76 (m, 4H), 2.68 (br d, 1H), 3.44-3.52 (m, 1H), 3.64 (s, 0.6H), 3.76 (s, 0.4H), 4.25 (s, 0.6H), 4.33 (s, 0.4H), 7.88 (d, 1.2H), 7.90 (br s, 2H), 7.92 (d, 0.8H), 8.31 (d, 0.8H), 8.53 (d, 1.2H), 9.00 (d, 1H), 10.43 (s, 0.4H) and 10.86 (s, 0.6H) ppm; MS (ES+) 484.3 Compound IA-217 (25)-N-[5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]pyrrolidine-2-carboxamide 1H NMR (400.0 MHz, DMSO) d 1.18 (d, 6H), 1.67-1.72 (m, 1H), 2.04-2.21 (m, 2H), 3.00 (br s, 2H), 3.35-3.41 (m, 1H), 3.45-3.59 (m, 3H), 4.28-4.34 (m, 1H), 7.82 (br s, 2H), 7.88-7.92 (m, 2H), 8.44-8.53 (m, 2H), 9.00-9.01 (2×s, 1H) and 10.87 (s, 1H) ppm; MS (ES+) 458.3

Sources & evidence

ORD record: ord-91a3185a02d345afa0a928ca5d4a3606
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365557B2

Reaction notes

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