Cyclopentylamine → HCID 10217358, compound

HRID 1296712Notes

Reaction equation

HRID 1296712 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[N:18]=3)=[C:15]3[N:10]([C:11](SC)=[N:12][CH:13]=[CH:14]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=O.[CH:42]1([NH2:47])[CH2:46][CH2:45][CH2:44][CH2:43]1>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][CH:24]4[CH2:28][CH2:27][CH2:26][CH2:25]4)[N:18]=3)=[C:15]3[N:10]([C:11]([NH:47][CH:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[N:12][CH:13]=[CH:14]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 70297m-Chloroperbenzoic acidHCID 10151314HCID 10151314, compound

Product 1

HCID 10217358HCID 10217358, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of 4-[2-(3-chlorophenyl)-7-(methylthio)pyrazolo[1,5-c]pyrimidin-3-yl]-N-cyclopentylpyrimidin-2-amine (40 mg, 0.0915 mmol) in dichloromethane (3 mL) was added m-chloroperoxybenzoic acid (24 mg, 0.139 mmol). The reaction mixture was stirred 1.5 hours at 0° C. then diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic layer was washed with water and brine, then dried over magnesium sulfate. Filtration and concentration provided a crude oil which was heated in cyclopentylamine (2 mL, 20 mmol) at 85° C. in a sealed tube for 16 hours. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (4:1 to 3:1 hexanes:ethyl acetate) provided 2-(3-chlorophenyl)-N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]pyrazolo[1,5-c]pyrimidin-7-amine (28 mg, 65%) as a beige solid. Rf 0.27 (3:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.09 (d, 1H), 7.78 (d, 1H), 7.71 (s, 1H), 7.51–7.35 (m, 4H), 6.41 (d, 1H), 6.30 (d, 1H), 5.15 (d, 1H), 4.53 (m, 1H), 4.29 (m, 1H), 2.20 (m, 2H), 2.04 (m, 2H), 1.83–1.50 (m, 12 H); MS m/z 474 (M+1).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and concentration
  5. customprovided a crude oil which
  6. washwashed with saturated aqueous sodium bicarbonate solution
  7. washThe organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-6735f5ce981b45a38f19d1f8295893e0
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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