Dichloromethane → HCID 22329918, compound

HRID 272480Notes

Reaction equation

HRID 272480 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[N:16][C:17]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:30]([CH3:31])=[C:29]([Br:32])[C:28](=[O:33])[N:27]([CH:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[C:25]=4[N:26]=3)=[CH:18][CH:19]=2)[CH2:10][C:9]1([CH3:40])[CH3:39])=O)(C)(C)C.[Cl:41]CCl>Cl>[ClH:41].[Br:32][C:29]1[C:28](=[O:33])[N:27]([CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:25]2[N:26]=[C:21]([NH:20][C:17]3[CH:18]=[CH:19][C:14]([N:11]4[CH2:12][CH2:13][NH:8][C:9]([CH3:40])([CH3:39])[CH2:10]4)=[CH:15][N:16]=3)[N:22]=[CH:23][C:24]=2[C:30]=1[CH3:31]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 10196921HCID 10196921, compound

Product 1

HCID 22329918HCID 22329918, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-[6-(6-Bromo-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-2,2-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (0.051 g, 0.083 mmol) was dissolved in dichloromethane (3 mL) to which 2 N HCl (2 mL) was added and the resulting mixture was stirred at room temperature for 2 hours. This mixture was concentrated and allowed to sit for 10 days, it was then dissolved in 2 N HCl (2 mL) and stirred at room temperature for 5 hours. The solvent was removed to give 6-bromo-8-cyclopentyl-2-[5-(3,3-dimethyl-piperazin-1-yl)-pyridin-2-ylamino]-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride salt as a yellow solid (0.035 g, 71.4%). 1H NMR δ(400 MHz, DMSO-d6) 9.32 (s, 2H), 8.98 (s, 1H), 8.04 (d, J=2.7 Hz, 1H), 7.83 (d, J=9.3 Hz, 1H), 7.26 (m, 1H), 5.89 (m, 1H), 3.34 (m, 2H), 3.23 (m, 4H), 2.58 (s, 3H), 2.14 (m, 2H), 1.91 (m, 2H), 1.77 (m, 2H), 1.57 (m, 2H), 1.38 (s, 6H).

Workup

  1. additionwas added
  2. concentrationThis mixture was concentrated
  3. waitto sit for 10 days
  4. dissolutionit was then dissolved in 2 N HCl (2 mL)
  5. stirringstirred at room temperature for 5 hours
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-e43ba7ffa7df4a8a9a30290cca6d0ad5
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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