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

HRID 2094260Notes

Reaction equation

HRID 2094260 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-52141d37b4bf424cbc9b6372e01e71c2
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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