Hydrochloric Acid → 6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-8H-pyrido(2,3-d)pyrimidin-7-one

HRID 1271976Notes

Reaction equation

HRID 1271976 reaction equation
C(O[C:6](=O)[NH:7][CH:8]1[CH2:12][CH2:11][N:10]([C:13]2[CH:14]=[N:15][C:16]([NH:19][C:20]3[N:21]=[CH:22][C:23]4[C:29]([CH3:30])=[C:28]([C:31]([O:33]CC)=[CH2:32])[C:27](=[O:36])[N:26]([CH:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[C:24]=4[N:25]=3)=[CH:17][CH:18]=2)[CH2:9]1)(C)(C)C.Cl>C(Cl)(Cl)Cl>[C:31]([C:28]1[C:27](=[O:36])[N:26]([CH:37]2[CH2:41][CH2:40][CH2:39][CH2:38]2)[C:24]2[N:25]=[C:20]([NH:19][C:16]3[CH:17]=[CH:18][C:13]([N:10]4[CH2:11][CH2:12][N:7]([CH3:6])[CH2:8][CH2:9]4)=[CH:14][N:15]=3)[N:21]=[CH:22][C:23]=2[C:29]=1[CH3:30])(=[O:33])[CH3:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10196694(1-{6-[8-Cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 53302986-Acetyl-8-cyclopentyl-5-methyl-2-((5-(4-methylpiperazin-1-yl)pyridin-2-yl)amino)-8H-pyrido(2,3-d)pyrimidin-7-oneYield 76.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of (1-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (394 mg, 0.68 mmol) in chloroform (5 ml) was added hydrogen chloride (2 M ethereal solution, 2.0 ml, 4.0 mmol). The reaction mixture was stirred at RT for 12 h. The solvents were evaporated and the residue was dissolved in ethanol. The ethanol was evaporated to give 6-acetyl-8-cyclopentyl-5-methyl-2-[5-(4-methyl-piperazin-1-yl)-pyridin-2-ylamino]-8H-pyrido[2,3-d]pyrimidin-7-one (239 mg, 0.52 mmol). MS (APCI+) 487, 391, 279 (100); 1H NMR δ (400 MHz, DMSOd6) 8.98 (s, 1H), 8.34 (br, 2H), 7.78–7.73 (m, 2H), 7.51 (br, 1H), 5.89–5.80 (m, 1H), 3.98 (br, 2H), 3.62–3.51 (m, 4H), 2.40–3.23 (m, 2H), 2.44 (s, 3H), 2.25–2.20 (m, 2H), 2.16–2.13 (m, 1H), 1.93 (br, 2H), 1.80–1.78 (m, 2H), 1.61–1.58 (m, 2H); Anal. Calc'd for C24H29N7O2, 2.10 HCl, 2.85 H2O, 0.45 C2H5OH: C, 50.16; H, 6.68; N, 16.45; Cl−, 12.49. Found: C, 50.37; H, 6.90; N, 16.45; Cl−, 12.61.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in ethanol
  3. customThe ethanol was evaporated

Sources & evidence

ORD record
ord-02f5a8bcbb7540e888ef241691b6b7a2
Source dataset
uspto-grants-2007_04
Patent number
US07208489B2

Reaction notes

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