Cyclopentylamine → HCID 10456546, compound

HRID 859981Notes

Reaction equation

HRID 859981 reaction equation
[CH2:1]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:19]=2)=[C:11]2[CH:12]=[CH:13][CH:14]=[C:15](Cl)[N:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]1([NH2:35])[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH2:1]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[N:19]=2)=[C:11]2[CH:12]=[CH:13][CH:14]=[C:15]([NH:35][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2906CyclopentylamineHCID 10476315HCID 10476315, compound

Product 1

HCID 10456546HCID 10456546, compoundYield 32%

Procedure

A solution of 4-(2-benzyl-7-chloropyrazolo[1,5-a]pyridin-3-yl)-N-cyclopentyl-2-pyrimidinamine (65 mg, 0.16 mmol) in cyclopentylamine (2 mL, 20 mmol) was heated at 116° C. for 16 hours. The reaction mixture was cooled and the excess cyclopentylamine was removed in vacuo. The crude material was chromatographed (19:1 dichloromethane:acetone) to provide N-{4-[2-benzyl-7-(cyclopentylamino)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinyl}-N-cyclopentylamine (23 mg 32%) as a pale yellow solid. Rf 0.12 (5:1 hexanes:ethyl acetate); 1H NMR δ 8.18 (d, 1H), 7.59 (d, 1H), 7.30–7.10 (m, 6H), 6.65 (d, 1H), 5.99 (d, 1H), 4.59 (s, 2H), 4.30 (m, 1H), 3.98 (m, 1H), 2.21–2.00 (m, 4H), 1.90–1.50 (m, 12H); MS m/z 453 (M+1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe excess cyclopentylamine was removed in vacuo
  3. customThe crude material was chromatographed (19:1 dichloromethane:acetone)

Sources & evidence

ORD record
ord-5c3ed7f624e54b1faba41105f195c7f8
Source dataset
uspto-grants-2006_12
Patent number
US07153863B2

Reaction notes

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