Methanol → HCID 59379994, compound

HRID 2353678Notes

Reaction equation

HRID 2353678 reaction equation
C([S:4][CH2:5][C:6]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[N:9]=[C:8]([C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:27])=[CH:21][CH:20]=2)[N:7]=1)(=N)N.Br[CH:36]1[CH2:40][CH2:39][NH:38][C:37]1=[O:41].[OH-].[Na+].CO>CN(C=O)C.O>[CH3:18][C@H:13]1[CH2:14][O:15][CH2:16][CH2:17][N:12]1[C:10]1[CH:11]=[C:6]([CH2:5][S:4][CH:36]2[CH2:40][CH2:39][NH:38][C:37]2=[O:41])[N:7]=[C:8]([C:19]2[CH:20]=[CH:21][C:22]([NH:25][C:26]([NH:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:27])=[CH:23][CH:24]=2)[N:9]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 101034713-Bromopyrrolidin-2-oneHCID 59379877HCID 59379877, compound

Product 1

HCID 59379994HCID 59379994, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

1-[4-[4-(Carbamimidoylsulfanylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-3-phenyl-urea (125 mg) was dissolved in DMF (3 mL). The solution was then treated with 3-bromo-pyrrolidin-2-one (48 mg) followed by sodium hydroxide (42 mg) in water (1 mL), heated to 40° C. and left to stir for 24 h. The reaction was diluted in a little methanol and loaded onto a SCX-2 column (20 g), which was washed with methanol and the desired product eluted with 7N ammonia in methanol to give the desired material which was used without further characterisation.

Workup

  1. waitleft
  2. washwas washed with methanol
  3. washthe desired product eluted with 7N ammonia in methanol

Sources & evidence

ORD record
ord-dcefbca9148e45a9a9f359e08ec67f93
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

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