Ethanol → HCID 59380396, compound

HRID 2353844Notes

Reaction equation

HRID 2353844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29](/[CH:31]=[CH:32]/[C:33]([O:35]C)=[O:34])=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=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.C(O)C.[OH-].[Li+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:19]3[C:26]4[CH:27]=[CH:28][C:29](/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])=[CH:30][C:25]=4[S:24][C:20]=3[N:21]=[CH:22][N:23]=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

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 59380391HCID 59380391, compound

Product 1

HCID 59380396HCID 59380396, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyl (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino) [1]benzothieno[2,3-d]pyrimidin-7-yl]acrylate (100 mg, 0.19 mmol) in THF (3 vmL) were added ethanol (1 mL) and lithium hydroxide (2 N, 0.5 mL, 1 mmol, 5 equiv). The contents were stirred at rt for 16 h. The mixture was concentrated to dryness and the residue was triturated with ether and ethyl acetate to remove organic impurities. To the solid was added some water and 1N HCl to adjust the pH to ˜6. The solid was filtered and dried to obtain (2E)-3-[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acrylic acid (50 mg, 51%). 1H-NMR (DMSO-d6) δ 9.10 (s, 1H), 8.56 (d, 1H), 8.52 (s, 1H), 8.39 (d, 1H), 7.87 (dd, 1H), 7.74 (d, 1H), 7.42-7.59 (m, 3H), 7.30 (m, 2H), 7.23 (d, 1H), 7.17 (m, 1H), 6.69 (d, 1H), 5.26 (s, 2H); LCMS RT=3.77 min, [M+H]+=506.0.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. customthe residue was triturated with ether and ethyl acetate
  3. customto remove organic impurities
  4. additionTo the solid was added some water and 1N HCl
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-45775e8decd64ae9a5fbc56a758adb19
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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