Hydrochloric Acid → HCID 66549328, compound

HRID 1410061Notes

Reaction equation

HRID 1410061 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:38]=[CH:37][S:36][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=3)/[CH:21]=[CH:22]/[C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH-].[Na+].Cl>O1CCOCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:13]3[N:38]=[CH:37][S:36][C:14]=3[N:15]=[C:16]([C:18]3[CH:19]=[C:20]([CH:33]=[CH:34][CH:35]=3)/[CH:21]=[CH:22]/[C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68379353HCID 68379353, compound

Product 1

HCID 66549328HCID 66549328, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (E)-methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)styryl)benzoate (90 mg, 0.17 mmol) in 3 mL of 1,4-dioxane and 3 mL of H2O was added NaOH (140 mg, 3.5 mmol) at room temperature. Then the reaction was stirred at room temperature overnight and then treated by conc. HCl until pH=3-4. The solvent was removed under reduce pressure the residue was purified by preparative HPLC to give (E)-4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)styryl)benzoic acid (33 mg, 38%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 12.95 (brs, 1H), 10.09 (s, 1H), 9.38 (s, 1H), 8.37-8.30 (m, 2H), 7.82-7.78 (m, 3H), 7.47-7.32 (m, 5H), 6.92-6.78 (m, 3H), 3.81 (s, 3H), 3.80 (s, 3H). LC-MS: 511 [M+H]+, 509 [M−H]−, tR=1.71 min. HPLC: 99.30% at 214 nm, 99.65 at 254 nm, tR=4.98 min.

Workup

  1. customThe solvent was removed
  2. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-0b428bb3dceb45fdb624d4f33907361d
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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