Water → 4-[2-(4-fluorophenyl)-6-trifluoromethylpyrazolo[1,5-a]pyridin-3-yl]-N-(3-(4-methoxybenzyloxy)propyl)-2-pyrimidinamine

HRID 1374721Notes

Reaction equation

HRID 1374721 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]([C:21](=O)[CH:22]=[CH:23]N(C)C)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:19])([F:18])[F:17])=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[CH3:28][O:29][C:30]1[CH:44]=[CH:43][C:33]([CH2:34][O:35][CH2:36][CH2:37][CH2:38][NH:39][C:40]([NH2:42])=[NH:41])=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]([C:21]3[CH:22]=[CH:23][N:42]=[C:40]([NH:39][CH2:38][CH2:37][CH2:36][O:35][CH2:34][C:33]4[CH:32]=[CH:31][C:30]([O:29][CH3:28])=[CH:44][CH:43]=4)[N:41]=3)=[C:11]3[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:19])[F:18])=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 694231242-(4-Fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)-6-trifluoromethylpyrazolo[1,5-a]pyridineHCID 178491460HCID 178491460, compound

Product 1

HCID 210769724-[2-(4-fluorophenyl)-6-trifluoromethylpyrazolo[1,5-a]pyridin-3-yl]-N-(3-(4-methoxybenzyloxy)propyl)-2-pyrimidinamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)-6-trifluoromethyl-pyrazolo[1,5-a]pyridine (Example 65f. 2.0 g, 5.3 mmol), N-(3-(4-methoxybenzyloxy)propyl)-guanidine (2.7 g, 7.95 mmol), and potassium carbonate (2.2 g, 15.9 mmol) was stirred in N,N-dimethylformamide (20 mL) in a 100° C. oil bath for 18 h. The mixture was cooled to room temperature, water (200 mL) was added the mixture was extracted with chloroform. The chloroform extracts were dried over anhydrous MgSO4, filtered, and the solvent was evaporated. The crude material was purified by chromatography on silica gel using 30% EtOAc/hexanes as eluent to afford the title compound as a white solid, 2.1 g (72%). 1H NMR (acetone-d6) δ 9.18 (s, 1H), 8.67 (d, 1H, J=9.4 Hz), 8.15 (d, 1H, J=5.1 Hz), 7.77 (m, 2H), 7.56 (d, 1H, J=9.2 Hz), 7.34 (m, 4H), 6.90 (d, 2H, J=8.6 Hz), 6.50 (s, 1H), 6.38 (d, 1H, J=5.1 Hz), 4.49 (s, 2H), 3.80 (s, 3H), 3.63 (m, 4H), 1.98 (m, 2H). MS (+ve ion electrospray) 551 (30), (M+).

Workup

  1. extractionwas extracted with chloroform
  2. dry with materialThe chloroform extracts were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe crude material was purified by chromatography on silica gel using 30% EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-6a1bd7fc78c742ee95af11ceb6385556
Source dataset
uspto-grants-2007_01
Patent number
US07166597B2

Reaction notes

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