Dichloromethane → HCID 11168809, compound

HRID 272484Notes

Reaction equation

HRID 272484 reaction equation
C(OC([N:8]1[CH:13]([CH3:14])[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]([Br:33])[C:29](=[O:34])[N:28]([CH:35]5[CH2:39][CH2:38][CH2:37][CH2:36]5)[C:26]=4[N:27]=3)=[CH:19][CH:20]=2)[CH2:10][CH:9]1[CH3:40])=O)(C)(C)C.[Cl:41]CCl>Cl>[ClH:41].[Br:33][C:30]1[C:29](=[O:34])[N:28]([CH:35]2[CH2:36][CH2:37][CH2:38][CH2:39]2)[C:26]2[N:27]=[C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([N:11]4[CH2:12][CH:13]([CH3:14])[NH:8][CH:9]([CH3:40])[CH2:10]4)=[CH:16][N:17]=3)[N:23]=[CH:24][C:25]=2[C:31]=1[CH3:32]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 10312335HCID 10312335, compound

Product 1

HCID 11168809HCID 11168809, 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]-2,6-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 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-(3,5-dimethyl-piperazin-1-yl)-pyridin-2-ylamino]-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one hydrochloride salt as a yellow solid (0.039 g, 71.4%). 1H NMR δ(400 MHz, DMSO-d6) 9.51 (m, 1H), 9.02 (m, 1H),8.98 (s, 1H), 8.07 (s, 1H), 7.83 (s, 2H), 5.90 (m, 1H), 3.85 (d, J=11.2 Hz, 2H),3.35 (m, 2H), 2.76 (dd, J=12.0, 12.0 Hz 2H), 2.58 (s, 3H), 2.14 (m, 2H), 1.92 (m, 2H), 1.77 (m, 2H),1.58 (m, 2H), 1.28 (d, J=6.4 Hz, 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-74df3af9e2834af4aab9aef4a9fe1522
Source dataset
uspto-grants-2008_11
Patent number
US07456168B2

Reaction notes

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