Triethylamine → HCID 70654403, compound

HRID 2178190Notes

Reaction equation

HRID 2178190 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:21])=[C:6]([C@:8]2([CH:18]([F:20])[F:19])[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][C:10]([NH2:17])=[N:9]2)[CH:7]=1.C(N(CC)CC)C.[CH3:29][O:30][C:31]1[CH:52]=[CH:51][C:34]([C:35](Cl)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)=[CH:33][CH:32]=1>ClCCl>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([C:35]([NH:17][C:10]2[CH2:11][S:12](=[O:16])(=[O:15])[CH2:13][CH2:14][C@:8]([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=3[F:21])([CH:18]([F:19])[F:20])[N:9]=2)([C:34]2[CH:33]=[CH:32][C:31]([O:30][CH3:29])=[CH:52][CH:51]=2)[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 70654860HCID 70654860, compound

Product 1

HCID 70654403HCID 70654403, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-ylamine (318 mg, 826 μmol) and triethylamine (167 mg, 1.65 mmol) in dichloromethane (15 ml) was treated at 0° C. with 4,4′-dimethoxytritylchloride (336 mg, 991 μmol). The green reaction mixture was stirred at room temperature for 6 hours. Thereafter, the reaction mixture was evaporated, and the crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate 100:0 to 50:50 as the eluent. The [bis-(4-methoxy-phenyl)-phenyl-methyl]-[(S)-5-(5-bromo-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-yl]-amine (365 mg, 63% yield) was obtained as a grey foam. MS (ISP): m/z=687.0 [M+H]+and 689.3 [M+2+H]+.

Workup

  1. customThereafter, the reaction mixture was evaporated
  2. customthe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate 100:0 to 50:50 as the eluent

Sources & evidence

ORD record
ord-abac51d0ee764b89bec9d49fd800f3c2
Source dataset
uspto-grants-2015_06
Patent number
US09067924B2

Reaction notes

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