Cyclopropylamine → HCID 10237661, compound

HRID 1269076Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]4[CH2:22][CH2:21][CH2:20][CH2:19]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>C(OCC)(=O)C>[CH:18]1([NH:17][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)=[N:8][N:7]4[C:2]([NH:31][CH:28]5[CH2:30][CH2:29]5)=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[CH:15][N:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

Conditions

Temperature: 100 °C

Procedure

4-[7-Chloro-2-(2-furyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (100 mg, 0.26 mmol) and cyclopropylamine (5 mL) were put in a steel bomb. After heating at 100° C. for 3 days, the reaction was allowed to cool to room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and brine, then dried over magnesium sulfate. Filtration and concentration followed by purification with flash chromatography (3:7 ethyl acetate:hexanes) gave 3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-cyclopropyl-2-(2-furyl)pyrazolo[1,5-a]pyridin-7-amine (34 mg, 32%) as a yellow foam. 1H NMR (CDCl3): δ 8.15 (d, 1H), 7.67 (d, 1H), 7.56 (d, 1H), 7.30 (t, 1H), 6.86 (d, 1H), 6.57 (d, 1H), 6.52 (m, 1H), 6.36 (d, 1H), 6.32 (s, 1H), 5.14 (d, 1H), 4.36 (m, 1H), 2.63 (m, 1H), 2.08 (m, 2H), 1.76–1.52 (m, 6H), 0.86 (m, 2H), 0.75 (m, 2H). MS m/401 (M+1).

Workup

temperatureto cool to room temperature
washwashed with water and brine
dry with materialdried over magnesium sulfate
filtrationFiltration and concentration
customfollowed by purification with flash chromatography (3:7 ethyl acetate:hexanes)

Sources & evidence

ORD record: ord-6f112d797a7c48e990a93f199fcdf38a
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199120B2

Reaction notes

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