Azepane → N-[3-(1-azepanyl)-1-phenylpropyl]-3-([1,1'-biphenyl]-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide

HRID 1964822Notes

Reaction equation

CS(O[CH2:6][CH2:7][C@H:8]([NH:15][C:16]([C@H:18]1[N:22]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:21][CH2:20][S:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)=O.[NH:38]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[N:38]1([CH2:6][CH2:7][CH:8]([NH:15][C:16]([CH:18]2[N:22]([S:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)=[CH:30][CH:31]=3)(=[O:24])=[O:25])[CH2:21][CH2:20][S:19]2)=[O:17])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

Reactant 2

HCID 8119Azepane

HCID 60036776(3S)-3-({[(2S)-3-([1,1'-biphenyl]-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)-3-phenylpropyl methanesulfonate2×

Product 1

HCID 60036768N-[3-(1-azepanyl)-1-phenylpropyl]-3-([1,1'-biphenyl]-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide

Procedure

Following the general method A as outlined in Example 16, starting from 3-({[3-([1,1′-biphenyl]-4-ylsulfonyl)-1,3-thiazolidin-2-yl]carbonyl}amino)-3-phenylpropyl methanesulfonate (Intermediate 9) and azepane, the title compound was obtained in 99.1% purity by HPLC.

Sources & evidence

ORD record: ord-7a3c287028d54d238c254509449755bf
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415480B2

Reaction notes

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