Sodium ethoxide → N-cyclopentyl-4-[2-(4-fluorophenyl)-6-(trifluoromethyl)-pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

HRID 2214943Notes

Reaction equation

HRID 2214943 reaction equation
Cl.[CH:2]1([NH:7][C:8]([NH2:10])=[NH:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.[O-]CC.[Na+].[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:34]([C:35](=O)[C:36]#[CH:37])=[C:25]3[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][N:24]3[N:23]=2)=[CH:18][CH:17]=1>C(O)C.O>[CH:2]1([NH:7][C:8]2[N:10]=[C:35]([C:34]3[C:22]([C:19]4[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=4)=[N:23][N:24]4[CH:29]=[C:28]([C:30]([F:32])([F:31])[F:33])[CH:27]=[CH:26][C:25]=34)[CH:36]=[CH:37][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 2723922Sodium ethoxideHCID 221748411-[2-(4-Fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-a]pyridin-3-yl]-2-propyn-1-oneHCID 178479367HCID 178479367, compound

Product 1

HCID 22174839N-cyclopentyl-4-[2-(4-fluorophenyl)-6-(trifluoromethyl)-pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamineYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of N-cyclopentylguanidine hydrochloride (2.20 g, 13.5 mmol) in ethanol (70 mL) was added sodium ethoxide (4.5 mL, 3 M in ethanol, 14 mmol). The mixture was stirred at room temperature for 30 minutes, then cooled to 0° C. To this mixture was added 1-[2-(4-fluorophenyl)-6-(trifluoromethyl)pyrazolo[1,5-α]pyridin -3-yl]-2-propyn-1-one (3.44 g, 10.4 mmol) portionwise The reaction mixture was stirred at 0° C. for 30 minutes, followed by room temperature for 15 hours. The reaction mixture was diluted with water (400 mL). The solid precipitate was collected on a filter to provide N-cyclopentyl-4-[2-(4-fluorophenyl)-6-(trifluoromethyl)-pyrazolo[1,5-α]pyridin-3-yl]-2-pyrimidinamine (4.48 g, 98%) as an orange solid. 1H NMR (400 MHz, CDCl3) δ 8.84 (s, 1H), 8.51 (d, 1H), 8.11 (d, 1H), 7.64 (dd, 2H), 7.44 (dd, 1H), 7.17 (t, 2H), 6.33 (d, 1H), 5.17 (d, 1H), 4.34(m, 1H), 2.15–2.06 (m, 2 H), 1.84–1.52 (m, 6H); 19F NMR (CDCl3): δ−62.70, −112.25 MS m/z 442 (M+1); mp 155–156° C.

Workup

  1. temperaturecooled to 0° C
  2. stirringwas stirred at 0° C. for 30 minutes
  3. waitfollowed by room temperature for 15 hours
  4. customThe solid precipitate was collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-254c2dfe724c40fb9fe5f7c5c435eb7a
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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