4-Aminopyrimidine → HCID 54269752, compound

HRID 1858177Notes

Reaction equation

HRID 1858177 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27]([OH:29])=O)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C[N:40](C)[CH2:41][CH2:42][CH2:43][N:44]=[C:45]=[N:46]CC.NC1C=CN=CN=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([C:27](=[O:29])[NH:40][C:41]3[CH:42]=[CH:43][N:44]=[CH:45][N:46]=3)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[S:33][C:34]([Cl:37])=[CH:35][CH:36]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 689584-AminopyrimidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22126044HCID 22126044, compound

Product 1

HCID 54269752HCID 54269752, compoundYield 40.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[2-(1-tert-butoxycarbonylpiperidin-2-yl)-ethoxy]-7-chloro-3-(5-chlorothiophen-2-yl)-2-oxo-1,2-dihydroquinoline-6-carboxylic acid (37 mg in 0.50 mL dry methylene chloride) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 37 mg) followed by 4-dimethylaminopyridine (8 mg) and 4-aminopyrimidine (18 mg) and the mixture stirred at room temperature. After 18 hours, the mixture was diluted with methylene chloride and washed with brine. The organic portion was concentrated in vacuo and the residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5+1% ammonium hydroxide) to give the title compound (17 mg).

Workup

  1. washwashed with brine
  2. concentrationThe organic portion was concentrated in vacuo
  3. customthe residue purified by flash chromatography on silica gel (methylene chloride:methanol, 95:5+1% ammonium hydroxide)

Sources & evidence

ORD record
ord-4cc907c992af4d679d7d4e2f6ff0af56
Source dataset
uspto-grants-2000_11
Patent number
US06150522

Reaction notes

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