1-(Morpholin-2-yl)methanamine → HCID 178523414, compound

HRID 1823793Notes

Reaction equation

HRID 1823793 reaction equation
OC1CC[N:5]([C:8]([NH:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([O:20][S:21]([C:24]4[CH:29]=[CH:28][C:27]([N:30]5[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]5)=[CH:26][CH:25]=4)(=[O:23])=[O:22])=[CH:19][C:13]=3[N:12]=2)=[O:9])[CH2:4][CH2:3]1.NC[CH:39]1[O:44][CH2:43][CH2:42][NH:41][CH2:40]1>O1CCCC1.CN1CCCC1=O>[N:41]1([CH2:3][CH2:4][NH:5][C:8](=[O:9])[NH:10][C:11]2[NH:15][C:14]3[CH:16]=[CH:17][C:18]([O:20][S:21]([C:24]4[CH:25]=[CH:26][C:27]([N:30]5[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32][CH2:31]5)=[CH:28][CH:29]=4)(=[O:23])=[O:22])=[CH:19][C:13]=3[N:12]=2)[CH2:42][CH2:43][O:44][CH2:39][CH2:40]1

Participants

5

Reactant 2

HCID 45420271-(Morpholin-2-yl)methanamineHCID 178522510HCID 178522510, compound

Product 1

HCID 178523414HCID 178523414, compoundYield 33.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 4-(4-hydroxy-piperidin-1-yl)-benzenesulfonic acid 2-[(4-hydroxy-piperidine-1-carbonyl)-amino]-1H-benzoimidazol-5-yl ester (example 79, 20 mg) and 2-(aminomethyl)-morpholine (50 mg) in tetrahydrofuran (1 ml) and N-methylpyrrolidinone (0.2 ml) was heated at 95° C. for 22 hours. The reaction mixture was then evaporated and purified by triggered LC/MS to give 4-(4-hydroxy-piperidin-1-yl)-benzenesulfonic acid 2-[3-(2-morpholin-4-yl-ethyl)-ureido]-1H-benzoimidazol-5-yl ester as an off-white solid (7 mg). Mass spectrum: 545 [M+H]+; retention time=5.47 minutes.

Workup

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

Sources & evidence

ORD record
ord-cdf7827b49824796968cd7e2e0fe2e00
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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