Bromoacetonitrile → HCID 68705709, compound

HRID 2353647Notes

Reaction equation

HRID 2353647 reaction equation
[C:1]([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](=[O:30])[N:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=2)[N:7]=1)(=N)N.BrC[C:33]#[N:34].[OH-].[Na+]>CN(C=O)C.O>[C:33]([CH2:1][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](=[O:30])[N:27]([CH3:28])[CH3:29])=[CH:21][CH:20]=2)[N:7]=1)#[N:34]

Participants

6

Reactant 3

HCID 11534BromoacetonitrileHCID 14798Sodium HydroxideHCID 59380034HCID 59380034, compound

Product 1

HCID 68705709HCID 68705709, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-[4-[4-(Carbamimidoylsulfanylmethyl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl]phenyl]-1,1-dimethyl-urea (0.38 mmol) was dissolved in DMF (2 mL). This was treated with bromoacetonitrile (0.030 mL) and then the sodium hydroxide (61 mg) in water (1 mL) and stirred at RT for 15 minutes. The reaction mixture was concentrated in vacuo and the residue loaded onto a SCX-2 column, washed with methanol and the desired material removed with 7N ammonia in methanol. The desired material was isolated and used without further chromatography.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with methanol
  3. customthe desired material removed with 7N ammonia in methanol

Sources & evidence

ORD record
ord-02f523789b10418491c21bf7ef2f4bda
Source dataset
uspto-grants-2010_07
Patent number
US07750003B2

Reaction notes

Loading…