Potassium Hydroxide → HCID 58346739, compound

HRID 222045Notes

Reaction equation

HRID 222045 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]3[C:24]4[CH2:32][CH2:31][C:30]5[C:26](=[CH:27][N:28]([CH2:33][C:34]([O:36]CC)=[O:35])[N:29]=5)[C:25]=4[S:39][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.[OH-].[K+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]3[C:24]4[CH2:32][CH2:31][C:30]5[C:26](=[CH:27][N:28]([CH2:33][C:34]([OH:36])=[O:35])[N:29]=5)[C:25]=4[S:39][C:22]=3[N:21]=[CH:20][N:19]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58346432HCID 58346432, compound

Product 1

HCID 58346739HCID 58346739, compoundYield 158.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent2×

Procedure

To THF/MeOH/H2O (150 mL, 10/1/1) cooled to 0° C. was added ethyl [6-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-4,5-dihydro-2H-pyrimido[5′,4′:4,5]thieno[2,3-e]indazol-2-yl]acetate (1673 mg, 2.7 mmol), followed by a solution of potassium hydroxide (1.2 g, 21.6 mmol) in THF/MeOH/H2O (20 mL, 10/1/1). The contents were stirred with warming to rt over 1 h, after which time the solvent was removed under reduced pressure. The crude residue was diluted with water (200 mL) which was vigorously stirred for 0.5 h, neutralized with aq. 1N HCl (12.0 mL) to pH=2-3. The contents were filtered to a light yellow solid, which was washed with water, and then hexanes. The collected product was dried in vacuo, to afford the final product (2.3 g, 99%) as a light yellow solid. 1H-NMR (DMSO-d6) δ 13.1 (br s, 1H), 8.44 (s, 1H), 8.36 (s, 1H), 7.95 (s, 1H), 7.77 (d, 1H), 7.52 (dd, 1H), 7.45 (dd, 1H), 7.14-7.33 (m, 4H), 5.24 (s, 2H), 4.92 (s, 2H), 3.39 (t, 2H), 2.95 (t, 2H); LCMS RT=3.32 min; [M+H]+=536.1.

Workup

  1. customafter which time the solvent was removed under reduced pressure
  2. additionThe crude residue was diluted with water (200 mL) which
  3. stirringwas vigorously stirred for 0.5 h
  4. filtrationThe contents were filtered to a light yellow solid, which
  5. washwas washed with water
  6. customThe collected product was dried in vacuo

Sources & evidence

ORD record
ord-b792f71c837a4639b3f6c8f2c6fe8803
Source dataset
uspto-grants-2012_06
Patent number
US08207172B2

Reaction notes

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