HCID 18446603, compound → Cyclopentylamine

HRID 1269057Notes

Reaction equation

HRID 1269057 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:22]4[CH:27]=[CH:26][N:25]=[C:24](NC(C)C)[CH:23]=4)=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:32]C1C=C(C2C(C3C=CN=C(S(C)=O)N=3)=C3C=CC=CN3N=2)C=CN=1>>[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([F:32])[CH:23]=4)=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 18446603HCID 18446603, compoundHCID 18446640HCID 18446640, compound

Product 2

HCID 2906CyclopentylamineHCID 18446639HCID 18446639, compound

Procedure

N-Cyclopentyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine. In a similar manner as described in example 17 from 2-(2-fluoro-4-pyridinyl)-3-[2-(methylsulfinyl)-4-pyrimidinyl]pyrazolo[1,5-a]pyridine (410 mg, 1.16 mmol) and cyclopentylamine (4 mL, 40.5 mmol) was formed crude N-cyclopentyl-4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (385 mg), of which 260 mg (0.694 mmol) was dissolved in isopropylamine (3 mL, 35.2 mmol) and heated at 150° C. in a steel bomb for 16 hours. The reaction mixture was cooled and the excess isopropylamine was removed under a stream of nitrogen to provide N-cyclopentyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine (170 mg, 52% for 2 step procedure) as a beige solid. 1H NMR (CDCl3) δ 8.50 (d, 1H), 8.41 (d, 1H), 8.13–8.08 (m, 2H), 7.32 (t, 1H), 6.92 (t, 1H), 6.80 (d, 1H), 6.62 (s, 1H), 6.47 (d, 1H), 5.26 (d, 1H), 4.63 (d, 1H), 4.34 (m, 1H), 3.85 (m, 1H), 2.11–2.04 (m, 2H), 1.79–1.51 (m, 6H), 1.22 (d, 6H); MS m/z 414 (M+1).

Sources & evidence

ORD record
ord-c712f250692d4b019a08be11051481bf
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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