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

HRID 551184Notes

Reaction equation

HRID 551184 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-methylsulphanylpropylamine 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-6ddf4953a1184101bbe88a14ade98bdc
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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