Hydrochloric Acid → HCID 11443379, compound

HRID 586507Notes

Reaction equation

HRID 586507 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:16]=[N:17][C:18]([NH:21][C:22]3[N:23]=[CH:24][C:25]4[C:31]([CH3:32])=[C:30]([C:33]([O:35]CC)=[CH2:34])[C:29](=[O:38])[N:28]([CH:39]5[CH2:43][CH2:42][CH2:41][CH2:40]5)[C:26]=4[N:27]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:44]>C(Cl)(Cl)Cl>[ClH:44].[C:33]([C:30]1[C:29](=[O:38])[N:28]([CH:39]2[CH2:43][CH2:42][CH2:41][CH2:40]2)[C:26]2[N:27]=[C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([N:11]4[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]4)=[CH:16][N:17]=3)[N:23]=[CH:24][C:25]=2[C:31]=1[CH3:32])(=[O:35])[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10196796HCID 10196796, compound

Product 1

HCID 11443379HCID 11443379, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution 4-{6-[8-cyclopentyl-6-(1-ethoxy-vinyl)-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-[1,4]diazepane-1-carboxylic acid tert-butyl ester (116 mg, 0.20 mmol) in chloroform (5 mL) was added hydrogen chloride (2 M ethereal solution, 5.0 mL, 10.0 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-2-(5-[1,4]diazepan-1-yl-pyridin-2-ylamino)-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride salt (47 mg, 0.10 mmol). MS (APCI+) 432, 462 (M+1, 100); 1H NMR δ (400 MHz, DMSO-d6) 9.19 (br, 2H), 8.99 (s, 1H), 7.91 (s, 1H), 7.78-7.75 (m, 2H), 5.88-5.80 (m, 1H), 3.80-3.77 (m, 3H), 3.25 (br, 3H), 3.16 (br, 2H), 2.44 (s, 3H), 2.34 (s, 3H), 2.49-2.18 (m, 2H), 2.12-2.10 (m, 2H), 1.93 (br, 2H), 1.81-1.78 (m, 2H), 1.61-1.58 (m, 2H); Anal. Calc'd for C25H31N7O2, 2.80 HCl, 0.45 C3H8O2: C, 53.35; H, 6.25; N, 16.25. Found: C, 52.96; H, 6.62; N, 15.95.

Workup

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

Sources & evidence

ORD record
ord-d17c605499ed49e4aa76fe63c04da174
Source dataset
uspto-grants-2005_08
Patent number
US06936612B2

Reaction notes

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