2-Methoxyethylamine → HCID 10274307, compound

HRID 861157Notes

Reaction equation

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

Participants

Reactant 2

HCID 80182-Methoxyethylamine

HCID 86596768HCID 86596768, compound

Product 1

HCID 10274307HCID 10274307, compoundYield 95%

Conditions

Temperature: 140 °C

Procedure

A mixture of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopropyl-2-pyrimidinamine (75 mg, 0.19 mmol) and 2-methoxyethylamine (5 mL, 58 mmol) was heated in a sealed tube at 140° C. for 24 hours. After cooling to room temperature, the mixture was concentrated. Flash chromatography (1:1 to 1:3 hexanes-ethyl acetate) provided 3-[2-(cyclopropylamino)-4-pyrimidinyl]-N-(2-methoxyethyl)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine (77.7 mg, 95%) as a yellow solid. 1H NMR (CDCl3): δ 8.03 (d, 1 H), 7.96 (d, 1 H), 7.60 (d, 2 H), 7.31 (t, 1 H), 7.00 (d, 2 H), 6.41 (d, 1 H), 6.31 (t, 1 H), 6.04 (d, 1 H), 5.40 (broad, 1 H), 3.89 (s, 3 H), 3.72 (t, 2 H), 3.57 (q, 2 H), 3.43 (s, 3 H), 2.88 (m, 1 H), 0.88 (m, 2 H), 0.64 (m, 2 H); MS m/z 431 (M+1).

Workup

temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated

Sources & evidence

ORD record: ord-e3be7702d4fa422982dac676677716ba
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153855B2

Reaction notes

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