Cyclopentylamine → HCID 10407742, compound

HRID 859977Notes

Reaction equation

HRID 859977 reaction equation
CS[C:3]1[N:8]=[C:7]([C:9]2[C:10]([CH:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[OH:19])=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:6]=[CH:5][N:4]=1.ClC1C=C(C=CC=1)C(OO)=O.[CH:37]1([NH2:42])[CH2:41][CH2:40][CH2:39][CH2:38]1>ClCCl>[CH:37]1([NH:42][C:3]2[N:8]=[C:7]([C:9]3[C:10]([CH:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[OH:19])=[N:11][N:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=34)[CH:6]=[CH:5][N:4]=2)[CH2:41][CH2:40][CH2:39][CH2:38]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 70297m-Chloroperbenzoic acidHCID 10315728HCID 10315728, compound

Product 1

HCID 10407742HCID 10407742, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of {3-[2-(methylthio)pyrimidin-4-yl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (294 mg, 0.844 mmol) in dichloromethane (30 mL) was added m-chloroperoxybenzoic acid (218 mg, 1.26 mmol). The reaction mixture was stirred for 1.5 hours at 0° C., then diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate, then filtered and concentrated. The resulting solid was heated in cyclopentylamine (2 mL, 20 mmol) at 45° C. for 16 hours. Concentration and flash chromatography (59:1 dichloromethane:methanol) provided {3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-a]pyridin-2-yl}(phenyl)methanol (120 mg, 89%) as a light yellow solid. Rf 0.55 (29:1 dichloromethane:methanol); 1H NMR (CDCl3) δ 8.50 (d, 1H), 8.22 (d, 1H), 7.96 (br, 1H), 7.82 (d, 1H), 7.40 (d, 2H), 7.35–7.17 (m, 4H), 6.85 (t, 1H), 6.78 (d, 1H), 6.20 (s, 1H), 5.12 (s, 1H), 4.29 (m, 1H), 2.05 (m, 2H), 1.79–1.60 (m, 4H), 1.49 (m, 2H); MS m/z 386 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. concentrationConcentration and flash chromatography (59:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-a4f02416ff5e412caa4b9e866c812faf
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

Loading…