N-methyl-2-pyrrolidone → HCID 178523415, compound

HRID 1823791Notes

Reaction equation

HRID 1823791 reaction equation
CO[C:3]([NH:5][C:6]1[NH:10][C:9]2[CH:11]=[CH:12][C:13]([O:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)=[CH:21][CH:20]=3)(=[O:18])=[O:17])=[CH:14][C:8]=2[N:7]=1)=[O:4].NCC[CH:33]1[O:38][CH2:37][CH2:36][NH:35][CH2:34]1.C[N:40]1CC[CH2:42][C:41]1=O>O1CCCC1>[N:35]1([CH2:42][CH2:41][NH:40][C:3](=[O:4])[NH:5][C:6]2[NH:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][S:16]([C:19]4[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]5[CH2:28][CH2:29]5)=[CH:21][CH:20]=4)(=[O:18])=[O:17])=[CH:14][C:8]=3[N:7]=2)[CH2:34][CH2:33][O:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 41293182-MorpholineethanamineHCID 178502035HCID 178502035, compound

Product 1

HCID 178523415HCID 178523415, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 2-methoxycarbonylamino-3H-benzoimidazol-5-yl ester (example 67, 40 mg) and 2-(aminoethyl)-morpholine (125 mg) in tetrahydrofuran (2 ml) and N-methylpyrrolidinone (0.2 ml) was heated at 90° C. for 36 hours. The reaction mixture was then evaporated and purified by triggered LC/MS to give 4-(cyclopropylmethyl-amino)-benzenesulfonic acid 2-[3-(2-morpholin-4-yl-ethyl)-ureido]-1H-benzoimidazol-5-yl ester as an off-white solid (27 mg). Mass spectrum: 515 [M+H]+; retention time=5.97 minutes.

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by triggered LC/MS

Sources & evidence

ORD record
ord-e8db3c0806284de68716808c0d652916
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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