Sodium Bicarbonate → 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carboxylic acid tert-butyl ester

HRID 1244359Notes

Reaction equation

HRID 1244359 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12](=O)[CH:11]([NH:16][C:17]([C:19]2[S:20][C:21]3[C:27]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:26][CH:25]=[C:24]([O:34][CH3:35])[C:22]=3[N:23]=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:40].C(=O)(O)[O-].[Na+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[N:40]=[C:17]([C:19]3[S:20][C:21]4[C:27]([N:28]5[CH2:29][CH2:30][O:31][CH2:32][CH2:33]5)=[CH:26][CH:25]=[C:24]([O:34][CH3:35])[C:22]=4[N:23]=3)[NH:16][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 691841504-[(4-Methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-5-oxo-azepane-1-carboxylic acid tert-butyl ester

Product 1

HCID 112716912-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carboxylic acid tert-butyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.15 g 4-[(4-methoxy-7-morpholin-4-yl-benzothiazole-2-carbonyl)-amino]-5-oxo-azepane-1-carboxylic acid tert-butyl ester and 0.46 g ammonium acetate was melted at 120° C. for 3 hours and, after cooling to room temperature, suspended in a 1:1 mixture of water and saturated aqueous sodiumbicarbonate. Extraction with dichloromethane and chromatography on silicagel with dichloromethane/methanol 98:2 gave 0.10 g (72%) 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepine-6-carboxylic acid tert-butyl ester as yellow solid; M.p.: 142–144° C.; MS (ISP): m/e=486 (M+H+).

Workup

  1. customfor 3 hours
  2. extractionExtraction with dichloromethane and chromatography on silicagel with dichloromethane/methanol 98:2

Sources & evidence

ORD record
ord-ad4c48c6b3364c1aa12054a30ecafb7f
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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