Methanesulfonyl chloride → (+/-)5-[(3,5-Bis-trifluoromethyl-benzyl)-methanesulfonyl-amino]-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

HRID 2353981Notes

Reaction equation

[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14](C(=O)C)[CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C:9]2[CH:33]=[CH:34][CH:35]=[CH:36][C:8]1=2)=[O:6])([CH3:3])[CH3:2].[CH3:37][S:38](Cl)(=[O:40])=[O:39]>>[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([N:14]([CH2:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[S:38]([CH3:37])(=[O:40])=[O:39])[C:9]2[CH:33]=[CH:34][CH:35]=[CH:36][C:8]1=2)=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 113413065-[Acetyl-(3,5-bistrifluoromethylbenzyl)amino]-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylic acid isopropyl ester

Product 1

HCID 59003159(+/-)5-[(3,5-Bis-trifluoromethyl-benzyl)-methanesulfonyl-amino]-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

Procedure

The titled compound was prepared following the procedures described in Example 1 for the synthesis of 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester in step 8, by replacing acetic anhydride with methanesulfonyl chloride. MS (ES+): 553(M+).

Sources & evidence

ORD record: ord-c5565b159954431099b30e1836089110
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749992B2

Reaction notes

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