Phosgene → HCID 178522430, compound

HRID 1639622Notes

Reaction equation

HRID 1639622 reaction equation
[C:1](Cl)(Cl)=[O:2].[N:5]1([CH2:11][C:12]2[CH:26]=[CH:25][C:15]3[NH:16][C:17]([C:19]4[C:23]([NH2:24])=[CH:22][NH:21][N:20]=4)=[N:18][C:14]=3[CH:13]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH:27]1[CH2:32][CH2:31][S:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1.C(Cl)Cl>[N:5]1([CH2:11][C:12]2[CH:26]=[CH:25][C:15]3[NH:16][C:17]([C:19]4[C:23]([NH:24][C:1]([N:27]5[CH2:32][CH2:31][S:30][CH2:29][CH2:28]5)=[O:2])=[CH:22][NH:21][N:20]=4)=[N:18][C:14]=3[CH:13]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 6371Phosgene2×HCID 67164ThiomorpholineHCID 178508054HCID 178508054, compound

Product 1

HCID 178522430HCID 178522430, compound

Reagents, catalysts & solvents 1

HCID 21877217Toluene methylene chlorideSolvent

Procedure

Phosgene (20% in toluene) (0.3 ml) was added at 0° C. to a solution of 3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-ylamine (100 mg, 0.33 mmol) in a mixture of toluene/DCM (1:1). The reaction was stirred at ambient temperature for 1 hour then the excess phosgene was blown off by a stream of nitrogen. Thiomorpholine (35 mg, 0.33 mmol) was added and the reaction was stirred at ambient temperature for 1 hour then at 60° C. for 1 hour. The mixture was then concentrated in vacuo and the residue purified by preparative LC/MS to give thiomorpholine-4-carboxylic acid [3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-amide (LC/MS Polar: Rt 2.58, [M+H]+ 428).

Workup

  1. stirringthe reaction was stirred at ambient temperature for 1 hour
  2. waitat 60° C. for 1 hour
  3. concentrationThe mixture was then concentrated in vacuo
  4. customthe residue purified by preparative LC/MS

Sources & evidence

ORD record
ord-57e3fe3d753249538765caf5ba2f4b8b
Source dataset
uspto-grants-2012_02
Patent number
US08110573B2

Reaction notes

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