Methanol → HCID 69353735, compound

HRID 1827484Notes

Reaction equation

HRID 1827484 reaction equation
C[O:2][C:3](=[O:36])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:26]=[CH:27][C:28]3[CH:33]=[C:32]([CH3:34])[CH:31]=[C:30]([CH3:35])[N:29]=3)=[N:16][N:17]2[CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)=[CH:13][CH:12]=1.CO.[OH-].[K+]>C1COCC1.O>[CH3:34][C:32]1[CH:31]=[C:30]([CH3:35])[N:29]=[C:28]([CH:27]=[CH:26][C:15]2[C:14]3[C:18](=[CH:19][C:11]([NH:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[C:3]([OH:36])=[O:2])=[CH:12][CH:13]=3)[N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[N:16]=2)[CH:33]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 14797Potassium Hydroxide2×HCID 693539752-[3-[2-(4,6-Dimethyl-pyridin-2-yl)-vinyl]-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid methyl ester

Product 1

HCID 69353735HCID 69353735, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 2-[3-[2-(4,6-Dimethyl-pyridin-2-yl)-vinyl]-1-(tetrahydro-pyran-2-yl)-1H-indazol-6-ylamino]-benzoic acid methyl ester (1.98 g, 4.11 mmol) in THF:MeOH (12 ml, 3:1) was added Potassium hydroxide (1.15 g, 20.5 mmol) dissolved in H2O (3 ml). The reaction was heated at 70° C. for 2 hr, cooled, concentrated under reduced pressure to about 5 ml and diluted with more water. The solution was neutralized with 2N HCl and the precipitate was collected by filtration and washed with water to give 2.00 g (quantitative) of a bright yellow solid. 1H NMR (DSMO-d6) δ 513.12 (1H, broad s), 9.82 (1H, s), 8.13 (1H, d, J=8.7 Hz), 7.95 (1H, dd, J=1.5, 8.0 Hz), 7.89 (1H, d, J=16.4 Hz), 7.60 (1H, s), 7.50 (1H, d, J=16.4 Hz), 7.46 (1H, d, J=6.9 Hz), 7.37 (1H, d, J=7.7 Hz), 7.20 (1H, d, J=8.7 Hz), 7.06 (1 H, s), 6.86 (1H, t, J=6.9 Hz), 5.85 (1H, d, J=7.3 Hz), 3.82 (2H, m), 2.50 (3H, s, obscured by dmso), 2.48 (2H, m), 2.34 (3H, s), 2.03 (2H, m), 1.76 (1H, m), 1.59 (2H, m). Anal. Calcd for C28H28N4O3.0.5 KOH: C, 67.72; H, 5.79; N, 11.28.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure to about 5 ml
  3. additiondiluted with more water
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customto give 2.00 g (quantitative) of a bright yellow solid

Sources & evidence

ORD record
ord-9c5394c4c1fd4d6bab156f77dc867712
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

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