Water → 4-Hydroxy-5-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-azepane-1-carboxylic acid tert-butyl ester

HRID 1244357Notes

Reaction equation

HRID 1244357 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([OH:14])=O)[S:11][C:7]=2[C:6]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]([O:37][C:38]([N:40]1[CH2:46][CH2:45][CH:44]([OH:47])[CH:43]([NH2:48])[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].O>CN(C)C=O>[C:33]([O:37][C:38]([N:40]1[CH2:41][CH2:42][CH:43]([NH:48][C:12]([C:10]2[S:11][C:7]3[C:6]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=3[N:9]=2)=[O:14])[CH:44]([OH:47])[CH2:45][CH2:46]1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 219192164-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acidHCID 58717039tert-Butyl trans-4-amino-5-hydroxyazepane-1-carboxylate

Product 1

HCID 691841154-Hydroxy-5-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-azepane-1-carboxylic acid tert-butyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g 4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid and 0.31 g 1,1′-carbonyl-diimidazole in 25 ml dimethylformamide were stirred at room temperature for 16 hours. 0.43 g 4-amino-5-hydroxy-azepane-1-carboxylic acid tert-butyl ester were added and stirring was continued for 16 hours at room temperature. Water was added and the mixture was extracted with ethylacetate. Chromatography on silicagel with dichloromethane/methanol 98:2 yielded 0.68 g (79%) 4-hydroxy-5-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-azepane-1-carboxylic acid tert-butyl ester as a yellow solid; M.p.: 71–73° C.; MS (ISP): m/e=507 (M+H+).

Workup

  1. extractionthe mixture was extracted with ethylacetate

Sources & evidence

ORD record
ord-b7152cad6bec434880a814d8e0fe4374
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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