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Triethylamine → N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

HRID 610811
Notes
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Reaction equation

HRID 610811 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1.Cl.CN.[CH2:30]([N:32](CC)CC)C>C(O)C>[CH3:30][NH:32][C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:5]=[C:4]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:26])[CH3:25])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 10644414N-[4-(6-chloro-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

Product 1

HCID 54406992N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamideYield 44%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
140 °C

Procedure

0.62 g (0.00175 mol) of N-[4-(6-chloro-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide was dissolved in 20 ml of ethanol, treated with 1.36 g (0.0201 mol) of methylamine hydrochloride and 5.3 ml (0.038 mol) of triethylamine and stirred in an autoclave at 140° C. for 17 hours. The mixture was freed completely from solvent, the residue was partitioned in ethyl acetate/water and filtered off under suction. There was obtained 0.30 g (44%) of N-[4-(6-methylamino-2-pyrrolidin-1-yl-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide as beige crystals; m.p. 271-274° C.

Workup

  1. customthe residue was partitioned in ethyl acetate/water
  2. filtrationfiltered off under suction

Sources & evidence

ORD record
ord-2fd68edbe8ec44ca834108309f339adb
Source dataset
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05998665

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes