Chloroform → HCID 10128284, compound

HRID 272419Notes

Reaction equation

HRID 272419 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:35](=[O:36])[N:34]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:9]2[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]4)=[CH:17][N:16]=3)[N:12]=[CH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2].C(Cl)(Cl)[Cl:43]>C(O)C>[ClH:43].[CH2:1]([O:3][C:4]([C:6]1[C:35](=[O:36])[N:34]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:9]2[N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]4)=[CH:17][N:16]=3)[N:12]=[CH:13][C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 11238371HCID 11238371, compound

Product 1

HCID 10128284HCID 10128284, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[5-(4-tert-Butoxycarbonyl-piperazin-1-yl)-pyridin-2-ylamino]-8-cyclopentyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.40 g, 0.709 mmol, prepared as in Example 6) was dissolved in a mixture of chloroform (15 ml) and ethanol (15 ml) and the solution was purged with anhydrous hydrogen chloride gas. After 2 hours, the addition of ethyl acetate precipitated a solid which was filtered, washed with diethyl ether and dried in vacuo to yield 0.4 g of 8-cyclopentyl-7-oxo-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester hydrochloride as a yellow solid. MS (APCI); M++1: Calc'd, 464.53. Found, 464.4. Analyses for C24H29N7O3.0.75H2O.2.0HCl: Calc'd: C, 52.41; H, 5.96; N, 17.83, Cl (ionic), 12.89; H2O, 2.46. Found: C, 52.25; H, 5.86; N, 17.85; Cl (ionic), 12.10 ; H2O, 1.52.

Workup

  1. customthe solution was purged with anhydrous hydrogen chloride gas
  2. additionthe addition of ethyl acetate
  3. customprecipitated a solid which
  4. filtrationwas filtered
  5. washwashed with diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4a2c554f9a83401d90d06278aeddf9b1
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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