Isopropylamine → HCID 18446644, compound

HRID 1269053Notes

Reaction equation

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

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 18446643HCID 18446643, compound

Product 1

HCID 18446644HCID 18446644, compoundYield 80.7%

Procedure

A solution of N-cyclopropyl-4-[2-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine (206 mg, 0.595 mmol) in isopropylamine (3 mL, 35.2 mmol) was heated at 150° C. in a steel bomb for 16 hours. The excess isopropylamine was removed under a stream of nitrogen. The crude material was triturated with ether to provide N-cyclopropyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine (185 mg, 80%) as a tan solid. 1H NMR (CDCl3) δ 8.60 (d, 1H), 8.51 (d, 1H), 8.14 (m, 2H), 7.32 (t, 1H), 6.93 (t, 1H), 6.80 (d, 1H), 6.62 (s, 1H), 6.55 (d, 1H), 5.62 (br, 1H), 4.60 (d, 1H), 3.87 (m, 1H), 2.85 (m, 1H), 1.29 (d, 3H), 1.22 (d, 3H), 0.86 (m, 2H), 0.63 (m, 2H); MS m/z 386 (M+1).

Workup

customThe excess isopropylamine was removed under a stream of nitrogen
customThe crude material was triturated with ether

Sources & evidence

ORD record: ord-9cd002c210bc40018f4cf061445f4d78
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199120B2

Reaction notes

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