2-Methoxyethylamine → 3-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-alpha]pyridin-5-amine

HRID 723996Notes

Reaction equation

HRID 723996 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]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:4]2[CH:3]=1.[CH3:30][O:31][CH2:32][CH2:33][NH2:34].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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]([F:29])=[CH:25][CH:24]=4)=[N:8][N:5]4[CH:6]=[CH:7][C:2]([NH:34][CH2:33][CH2:32][O:31][CH3:30])=[CH:3][C:4]=34)[CH:16]=[CH:15][N:14]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 102231334-[5-chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine

Product 1

HCID 102974023-[2-(Cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-alpha]pyridin-5-amine

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

4-[5-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-N-cyclopentyl-2-pyrimidinamine (0.1 g, 0.25 mmol) and 2-methoxyethylamine were treated with rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, cesium carbonate and palladium (II) acetate as described in Example 2 to give, after purification by flash chromatography (1:1 hexanes-ethyl acetate), 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-α]pyridin-5-amine (65 mg, 59%) as a solid. 1H-NMR (CDCl3): δ 8.2 (d, 1H), 7.9 (d, 1H), 7.55 (m, 2H), 7.4 (m, 1H), 7.1 (t, 2H), 6.32 (dd, 1H), 6.2 (d, 1H), 5.3 (broad s, 1H), 4.54 (t, 1H), 4.4 (m, 1H), 3.65 (m, 2H), 3.4 (s, 3H), 3.35 (m, 2H), 2.1 (m, 2H), 1.5–1.8 (m, 6H); 19F-NMR (CDCl3): δ −113.46; MS m/z 447 (M+1).

Workup

  1. customto give
  2. customafter purification by flash chromatography (1:1 hexanes-ethyl acetate), 3-[2-(cyclopentylamino)-4-pyrimidinyl]-2-(4-fluorophenyl)-N-(2-methoxyethyl)pyrazolo[1,5-α]pyridin-5-amine (65 mg, 59%) as a solid

Sources & evidence

ORD record
ord-0c4722db04974c95b0f18a6061fb5e8b
Source dataset
uspto-grants-2006_11
Patent number
US07141569B2

Reaction notes

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