Hydrochloric Acid → 6-acetyl-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride

HRID 272445Notes

Reaction equation

HRID 272445 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]3[N:23]=[CH:24][C:25]4[CH:31]=[C:30]([C:32](=[O:34])[CH3:33])[C:29](=[O:35])[N:28]([CH:36]5[CH2:40][CH2:39][CH2:38][CH2:37]5)[C:26]=4[N:27]=3)=[CH:19][CH:20]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO.C(Cl)Cl>[ClH:1].[C:32]([C:30]1[C:29](=[O:35])[N:28]([CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:26]2[N:27]=[C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([N:12]4[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]4)=[CH:16][N:17]=3)[N:23]=[CH:24][C:25]=2[CH:31]=1)(=[O:34])[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 114212634-[6-(6-Acetyl-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 113748126-acetyl-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Anhydrous HCl gas was bubbled through a solution of 4-[6-(6-acetyl-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3yl]-piperazine-1-carboxylic acid tert-butyl ester (398 mg, 0.74 mmol, prepared as in Example 32), in MeOH/CH2Cl2 (10 mL/10 mL) at room temperature for ˜5 min. The reaction mixture was stirred overnight and then solvent was removed under reduced pressure. The remaining solid was triturated with hot ethyl acetate and dried to provide 6-acetyl-8-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride (329 mg, 76%). mp >300° C. Anal. Calc'd for C23H27N7O2.4.25HCl: C, 46.94; H, 5.35; N, 16.66. Found: C, 46.77; H, 5.33; N, 16.30. M++1: Calc'd: 434.2. Found 434.2.

Workup

  1. customsolvent was removed under reduced pressure
  2. customThe remaining solid was triturated with hot ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-d41db336df57453e957262790d95fbee
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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