N-bromobutanimide → HCID 57826731, compound

HRID 1845693Notes

Reaction equation

HRID 1845693 reaction equation
CC([N:5]([CH2:9][C@@H:10]([NH:18][C:19]([C:21]1[S:22][C:23]([Cl:32])=[C:24]([C:26]2[N:30]([CH3:31])[N:29]=[N:28][CH:27]=2)[CH:25]=1)=[O:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)C(=O)[O-])(C)C.C1C(=O)N([Br:40])C(=O)C1>CN(C=O)C>[NH2:5][CH2:9][C@@H:10]([NH:18][C:19]([C:21]1[S:22][C:23]([Cl:32])=[C:24]([C:26]2[N:30]([CH3:31])[N:29]=[N:28][C:27]=2[Br:40])[CH:25]=1)=[O:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 86633571HCID 86633571, compound

Product 1

HCID 57826731HCID 57826731, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,1-dimethylethyl[(2S)-2-({[5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thienyl]carbonyl}amino)-3-cyclohexylpropyl]carbamate (140 mg, 0.29 mmol, prepared in Example 280) and NBS (103 mg, 0.58 mmol) in 2 mL of DMF was heated at 100° C. for 2 hours. The reaction mixture was purified by reverse phase HPLC (5-65% acetonitrile in H2O with 1% TFA) to give the title compound 14.1 mg (8%) as a white solid. LCMS (ES) m/z 462.0 (M+H)+, 1H NMR (400 MHz, METHANOL-d4) δppm 7.75 (s, 1H), 4.43 (m, 1H), 4.05 (s, 3H), 3.17 (m 1H), 3.05 (m, 1H), 2.00-0.90 (m, 13H).

Workup

  1. customThe reaction mixture was purified by reverse phase HPLC (5-65% acetonitrile in H2O with 1% TFA)

Sources & evidence

ORD record
ord-67b031cba27643f7bb988c0d329f7c7c
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

Loading…