HCID 10161966, compound → HCID 10207869, compound

HRID 1373820Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[C:10]([C:11]3[CH:16]=[C:15]([CH2:17][N:18]([CH3:20])[CH3:19])[N:14]=[C:13]([NH:21][CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1>C1(N)CCCC1.C(OCC)(=O)C>[CH:22]1([NH:21][C:2]2[N:7]3[N:8]=[C:9]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=4)[C:10]([C:11]4[CH:16]=[C:15]([CH2:17][N:18]([CH3:20])[CH3:19])[N:14]=[C:13]([NH:21][CH:22]5[CH2:26][CH2:25][CH2:24][CH2:23]5)[N:12]=4)=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-6-[(dimethylamino)methyl]-2-pyrimidinamine (60 mg, 0.13 mmol) in cyclopentylamine (2 mL) was heated in a sealed tube at 95° C. for 16 hours followed by heating at 100° C. for 72 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium bicarbonate solution. The organic layer was concentrated and chromatographed (37:3 dichloromethane:methanol) to provide N-cyclopentyl-3-{2-(cyclopentylamino)-6-[(dimethylamino)methyl]-4-pyrimidinyl}-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-amine (10 mg, 15%). 1H NMR (CDCl3) δ 7.70 (d, 1H), 7.65 (m, 2H), 7.31 (t, 1H), 7.12 (t, 2H), 6.37 (s, 1H), 6.05–5.95 (m, 2H), 5.13 (d, 1H), 4.35 (m, 1H), 4.01 (m, 1H), 3.20 (s, 2H), 2.20 (s, 6H), 2.15 (m, 2H), 2.05 (m, 2H), 1.90–1.50 (m, 12H); MS m/z 514 (M+1).

Workup

temperatureAfter cooling to room temperature
washwashed with a saturated aqueous sodium bicarbonate solution
concentrationThe organic layer was concentrated
customchromatographed (37:3 dichloromethane:methanol)

Sources & evidence

ORD record: ord-8997ef89a59a4609ad7bef340bbe9a7b
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163940B2

Reaction notes

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