Cyclopentylamine → HCID 22180919, compound

HRID 1796539Notes

Reaction equation

HRID 1796539 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[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][C:3]=1[C:30]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33].[CH:40]1([NH2:45])[CH2:44][CH2:43][CH2:42][CH2:41]1>>[CH:40]1([NH:45][C:2]2[N:7]3[N:8]=[C:9]([C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=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)[N:12]=4)=[C:6]3[CH:5]=[CH:4][C:3]=2[C:30]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])[O:31][CH2:32][CH3:33])[CH2:44][CH2:43][CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 21948668HCID 21948668, compound

Product 1

HCID 22180919HCID 22180919, compoundYield 96.1%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-[7-chloro-2-(4-fluorophenyl)-6-(triethoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (2.37 g, 4.28 mmol) and cyclopentylamine (10 mL, 100 mmol) was heated in a sealed tube at 80° C. for 16 hours. The reaction mixture was cooled to room temperature and excess cyclopentylamine was removed in vacuo. The crude solid was triturated in water. The solids were collected on a filter to provide N-cyclopentyl-3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-6-(triethoxymethyl)pyrazolo[1,5-a]pyridin-7-amine (2.48 g, 96%). Rf 0.42 (4:1 hexanes:ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.04 (d, 1H), 7.75 (d, 1H), 7.68–7.60 (m, 3H), 7.12 (t, 2H), 6.36–6.31 (m, 2H), 5.30 (m, 1H), 5.07 (d, 1H), 4.53 (m, 1H), 3.45 (q, 6H), 2.12–1.95 (m, 4H), 1.80–1.45 (m, 12H), 1.25 (t, 9H); MS m/z 603 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customexcess cyclopentylamine was removed in vacuo
  3. customThe crude solid was triturated in water
  4. customThe solids were collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-d479c332f696470eaca89d91b7b52b19
Source dataset
uspto-grants-2006_04
Patent number
US07030134B2

Reaction notes

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