4-(Morpholin-3-on-4-yl)-3-nitro-benzoic acid chloride → HCID 178503702, compound

HRID 2222483Notes

Reaction equation

HRID 2222483 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([C@@H:9]([NH2:14])[CH2:10][CH2:11][S:12][CH3:13])=[N:8][C:4]=2[CH:3]=1.[N:17]1([C:24]2[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][C:25]=2[N+:33]([O-:35])=[O:34])[CH2:22][CH2:21][O:20][CH2:19][C:18]1=[O:23]>C1COCC1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([C@@H:9]([NH:14][C:28](=[O:29])[C:27]3[CH:31]=[CH:32][C:24]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][C:18]4=[O:23])=[C:25]([N+:33]([O-:35])=[O:34])[CH:26]=3)[CH2:10][CH2:11][S:12][CH3:13])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 860694074-(Morpholin-3-on-4-yl)-3-nitro-benzoic acid chlorideHCID 178503691(S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulfanylpropylamine

Product 1

HCID 178503702HCID 178503702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

237 mg (0.93 mmol) of (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methylsulphanyl-propylamine are dissolved with 0.257 ml TEA in 10 ml THF and a solution of 290 mg (1.02 mmol) 4-(morpholin-3-on-4-yl)-3-nitro-benzoic acid chloride in 10 ml THF is added dropwise. The reaction mixture is stirred for 16 hours at ambient temperature and then evaporated down i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol 100:0->95:5).

Workup

  1. customevaporated down i
  2. customThe residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol 100:0->95:5)

Sources & evidence

ORD record
ord-3b83262293284fa78253c636f4cc57ed
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

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