Hydrochloric Acid → HCID 11443379, compound

HRID 272475Notes

Reaction equation

HRID 272475 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, 2.80HCl, 0.45C3H8O2: 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-1f82a27a36624917a8feffd2621706b1
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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