2-Methoxyethylamine → HCID 10139327, compound

HRID 861155Notes

Reaction equation

HRID 861155 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=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)[N:12]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1.[CH3:31][O:32][CH2:33][CH2:34][NH2:35]>>[CH:18]1([NH:17][C:13]2[N:12]=[C:11]([C:10]3[C:9]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)=[N:8][N:7]4[C:2]([NH:35][CH2:34][CH2:33][O:32][CH3:31])=[CH:3][CH:4]=[CH:5][C:6]=34)[CH:16]=[CH:15][N:14]=2)[CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 57444748HCID 57444748, compound

Product 1

HCID 10139327HCID 10139327, compoundYield 98%

Conditions

Temperature
90 °C

Procedure

A mixture of 4-[7-chloro-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (75 mg, 0.18 mmol) and 2-methoxyethylamine (5 mL, 58 mmol) was heated at 90° C. for 72 hours, then cooled and concentrated. Flash chromatography (1:1 to 1:3 hexanes-ethyl acetate) provided 3-[2-(cyclopentylamino)-4-pyrimidinyl]-N-(2-methoxyethyl)-2-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-7-amine (80.4 mg, 98%) as an off-white solid. 1H NMR (CDCl3): δ 7.98 (d, 1 H), 7.81 (d, 1 H), 7.59 (d, 2 H), 7.31 (t, 1 H), 6.99 (d, 2 H), 6.35–6.29 (m, 2 H), 6.03 (d, 1 H), 5.15 (broad, 1 H), 4.38 (m, 1 H), 3.89 (s, 3 H), 3.72 (t, 2 H), 3.57 (q, 2 H), 3.43 (s, 3 H), 2.09 (m, 2 H), 1.80–1.53 (m, 6 H); MS m/z 459 (M+1).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a2838534a6453c97d439f5bac898ef
Source dataset
uspto-grants-2006_12
Patent number
US07153855B2

Reaction notes

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