Benzoyl chloride, 2-chloro-4-[(5-fluoro-2-methylbenzoyl)amino]- → 2-(2-Hydroxyethyl)-5-[2-chloro-4-(2-methyl-5-fluorobenzoylamino)benzoyl]-1,5-benzothiazepine

HRID 2296761Notes

Reaction equation

HRID 2296761 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[S:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][CH:10]=1.[Cl:15][C:16]1[CH:24]=[C:23]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=2[CH3:34])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].C1(C2C=CC=CC=2C(NC2C=CC(C(Cl)=O)=CC=2)=O)C=CC=CC=1>>[OH:1][CH2:2][CH2:3][CH:4]1[CH:10]=[CH:9][N:8]([C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:23]([NH:25][C:26](=[O:35])[C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[CH3:34])=[CH:24][C:16]=2[Cl:15])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[S:5]1

Participants

4

Reactant 3

HCID 10639786Benzoyl chloride, 2-chloro-4-[(5-fluoro-2-methylbenzoyl)amino]-HCID 114505014-(2-Phenylbenzoylamino)-benzoylchlorideHCID 183874452-(2-Hydroxyethyl)-1,5-benzothiazepine

Product 1

HCID 183874502-(2-Hydroxyethyl)-5-[2-chloro-4-(2-methyl-5-fluorobenzoylamino)benzoyl]-1,5-benzothiazepine

Procedure

A mixture of 2-(2-hydroxyethyl)-1,5-benzothiazepine as prepared in Example 2 (0.070 g, 0.34 mM) and N,O-bis(tri-methylsilyl)acetamide (0.15 ml, 0.67 mM)was treated as described in Example 3 with 2-Chloro-4-(2-methyl-5-fluorobenzoylamino)benzoyl chloride (0.11 g, 0.32 mM) substituted for 4-(2-phenylbenzoylamino)benzoyl chloride to give the product as a white solid. m/z (MH+) 500.

Workup

  1. additionwas treated

Sources & evidence

ORD record
ord-b787c0e1a6ec401c8e18f822f6e6ea72
Source dataset
uspto-grants-2002_12
Patent number
US06489321B1

Reaction notes

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