(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile → (2R,5S)-N1-((4S,7S,10aS)-7-Cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2-(4-fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-5-propylhexanediamide

HRID 529634Notes

Reaction equation

HRID 529634 reaction equation
[F:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][C@@H:7]([CH2:11][CH2:12][C@@H:13]([C:17](=[O:35])[NH:18][C@H:19]2[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[O:32][CH3:33])[C:20]2=[O:34])[CH2:14][CH2:15][CH3:16])[C:8](O)=[O:9])=[CH:4][CH:3]=1.[NH2:38][C@H:39]1[CH2:45][CH2:44][S:43][C@H:42]2[CH2:46][CH2:47][CH2:48][C@@H:49]([C:50]#[N:51])[N:41]2[C:40]1=[O:52]>>[C:50]([C@H:49]1[N:41]2[C@@H:42]([S:43][CH2:44][CH2:45][C@H:39]([NH:38][C:8](=[O:9])[C@@H:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:37][CH:36]=3)[CH2:11][CH2:12][C@H:13]([CH2:14][CH2:15][CH3:16])[C:17]([NH:18][C@H:19]3[CH2:25][CH2:24][CH2:23][CH2:22][N:21]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[O:32][CH3:33])[C:20]3=[O:34])=[O:35])[C:40]2=[O:52])[CH2:46][CH2:47][CH2:48]1)#[N:51]

Participants

3

Reactant 2

HCID 68292315(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrileHCID 68311019(2R,5S)-2-(4-Fluorobenzyl)-5-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-ylcarbamoyl)octanoic acid

Product 1

HCID 86706264(2R,5S)-N1-((4S,7S,10aS)-7-Cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2-(4-fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-5-propylhexanediamide

Procedure

(2R,5S)—N1-((4S,7S,10aS)-7-Cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-yl)-2-(4-fluorobenzyl)-N6-((S)-1-(2-methoxyphenyl)-2-oxoazepan-3-yl)-5-propylhexanediamide was synthesized as described in General Procedure H using Intermediate 76 (8.5 mg, 0.017 mmol) and Intermediate 36 (5.0 mg, 0.019 mmol) to give a white solid (5.9 mg, 49% yield). Anal. Calcd. for C39H50FN5O5S m/z 719.7. found: 720.3 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.37 (1H, d, J=6.6 Hz), 7.33-7.25 (1H, m), 7.09-7.02 (3H, m), 7.01-6.94 (3H, m), 6.86 (2H, t, J=8.8 Hz), 5.54-5.32 (3H, m), 5.29 (1H, d, J=4.9 Hz), 5.06-4.86 (2H, m), 4.04-3.89 (1H, m), 3.83 (3H, s), 3.54-3.35 (1H, m), 3.10-2.88 (1H, m), 2.80-2.54 (3H, m), 2.41-2.29 (1H, m), 2.21-1.18 (21H, m), 0.93-0.82 (3H, m).

Sources & evidence

ORD record
ord-fe9cf815dc2b4cb087a2e2735ac44307
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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