Water → HCID 25252994, compound

HRID 604359Notes

Reaction equation

HRID 604359 reaction equation
CS([C:5]1[N:6]=[CH:7][C:8]2[C:17]3[CH:16]=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]=3[N:11]=[C:10]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:9]=2[N:28]=1)(=O)=O.[CH:29]1([NH2:32])[CH2:31][CH2:30]1.O>CN1C(=O)CCC1>[CH:29]1([NH:32][C:5]2[N:6]=[CH:7][C:8]3[C:17]4[CH:16]=[CH:15][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]=4[N:11]=[C:10]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C:9]=3[N:28]=2)[CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 962WaterHCID 69828CyclopropylamineHCID 25252991HCID 25252991, compound

Product 1

HCID 25252994HCID 25252994, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

methyl 3-(methylsulfonyl)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate (1.0 eq, 117 mg, 0.298 mmol) was mixed in a vial with cylopropylamine (3.0 eq, 62 ul, 0.89 mmol) in NMP (2 ml). The mixture was stirred at 60° C. for 50 minutes. Water was added and the resulting solid filtered. The material was suspended in AcOEt/hexanes and filtered to afford methyl 3-(cyclopropylamino)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate as a yellow solid (86 mg, 78% yield). LCMS (ES): >95% pure, m/z 371 [M+1]+.

Workup

  1. filtrationthe resulting solid filtered
  2. filtrationfiltered

Sources & evidence

ORD record
ord-69a51928833d4b9cb8250a1f756944b1
Source dataset
uspto-grants-2011_03
Patent number
US07910600B2

Reaction notes

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