Cyclopentylamine → HCID 10288486, compound

HRID 1269086Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[N:24]=[C:25]([CH3:28])[S: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)[CH:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH:29]1([NH2:34])[CH2:33][CH2:32][CH2:31][CH2:30]1>C(OCC)(=O)C>[CH:29]1([NH:34][C:2]2[N:7]3[N:8]=[C:9]([C:23]4[N:24]=[C:25]([CH3:28])[S:26][CH:27]=4)[C:10]([C:11]4[CH:16]=[CH:15][N:14]=[C:13]([NH:17][CH:18]5[CH2:22][CH2:21][CH2:20][CH2:19]5)[CH:12]=4)=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-[7-chloro-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyridinamine from previous reaction was added cyclopentylamine and the resulting mixture heated to 80° C. for 3 days. The resultant solution was cooled to room temperature, diluted with ethyl acetate and washed with water, brine and dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (1:19 methanol/dichloromethane) gave N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyridinyl]-2-(2-methyl-1,3-thiazol-4-yl)pyrazolo[1,5-a]pyridin-7-amine (20 mg, 120% for two steps) as a brown foam. 1H NMR (CDCl3): δ 8.09 (d, 1H), 7.56 (d, 1H), 7.34 (s, 1H), 7.15 (t, 1H), 6.98 (d, 1H), 6.64 (d, 1H), 6.45 (s, 1H), 5.60 (d, 1H), 4.80 (b, 1H), 3.94 (m, 1H), 3.87 (m, 1H), 2.76 (s, 3H), 1.98–1.45 (m, 16H). MS m/z 459 (M+1).

Workup

washwashed with water, brine
dry with materialdried over magnesium sulfate
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-ce6e39771baf4387b7b8a95092d2d8d7
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199120B2

Reaction notes

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