tert-butyl N-(2-oxoethyl)carbamate → HCID 86656933, compound

HRID 411019Notes

Reaction equation

HRID 411019 reaction equation
Cl.Cl.[NH:3]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([NH:18][C:19]4[S:20][C:21]5[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:22]=5[N:23]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1.[C:32]([O:36][C:37](=[O:42])[NH:38][CH2:39][CH:40]=O)([CH3:35])([CH3:34])[CH3:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:32]([O:36][C:37](=[O:42])[NH:38][CH2:39][CH2:40][N:3]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[CH:31]=[CH:30][C:14]3[N:15]([CH3:29])[C:16]([NH:18][C:19]4[S:20][C:21]5[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:22]=5[N:23]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1)([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydrideHCID 86656934HCID 86656934, compound

Product 1

HCID 86656933HCID 86656933, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(3-{[2-(6-Chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carbonyl]amino}-pyrrolidin-1-yl)-ethyl]-carbamic acid tert-butyl ester (56 mg) was prepared by following General Procedure P starting from 2-(6-chloro-benzothiazol-2-ylamino)-1-methyl-1H-benzoimidazole-5-carboxylic acid pyrrolidin-3-ylamide dihydrochloride (84 mg), (2-oxo-ethyl)-carbamic acid tert-butyl ester (40 mg), and Na(OAc)3BH (65 mg) in DCM (2 mL).

Sources & evidence

ORD record
ord-f806454d927248fe87b9cfcd22c7ed98
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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