Sodium Hydroxide → 4-Bromo-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-alpha]pyridin-5-amine

HRID 724009Notes

Reaction equation

HRID 724009 reaction equation
[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:9]3[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:35]N1C(=O)CCC1=O.[OH-].[Na+]>ClCCl>[Br:35][C:8]1[C:9]2[N:10]([N:13]=[C:14]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]3[CH2:24][CH2:25][CH2:26][CH2:27]3)[N:17]=2)[CH:11]=[CH:12][C:7]=1[NH:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 10276099N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-pyrazolo[1,5-a]pyridin-5-amine

Product 1

HCID 102802404-Bromo-N-cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo[1,5-alpha]pyridin-5-amineYield 84.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Cyclopentyl-3-[2-(cyclopentylamino)pyrimidin-4-yl]-2-(4-fluorophenyl)pyrazolo-[1,5-α]pyridin-5-amine (100 mg, 0.22 mmol) was dissolved in dichloromethane (5 mL) and treated with N-bromosuccinimide (40 mg, 0.22 mmol). The reaction mixture was stirred for 10 minutes. Additional dichloromethane and 1N aqueous sodium hydroxide was added. The phases were separated, the organic phase washed with water, dried (magnesium sulfate), filtered and concentrated to dryness to give 100 mg of the title compound as a yellow foam. 1H NMR (CDCl3): δ 8.32 (d, 1H), 8.22 (d, 1H), 7.53 (q, 2H), 7.04 (t, 2H), 6.53 (m, 2H), 5.17 (d, 1H), 4.72 (d, 1H), 4.33 (m, 1H), 3.95 (m, 1H), 2.1–1.4 (m, 16H); 19F NMR (CDCl3): δ −113.97; MS m/z 536 (M+1).

Workup

  1. customThe phases were separated
  2. washthe organic phase washed with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8539e760dbf542f9916c2f3153afbc7d
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

Loading…