Hydrochloric Acid → HCID 66549329, compound

HRID 1410064Notes

Reaction equation

HRID 1410064 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)[CH2:21][CH2:22][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)[CH2:21][CH2:22][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 68379391HCID 68379391, compound

Product 1

HCID 66549329HCID 66549329, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of methyl 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenethyl)benzoate (70 mg, 0.13 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 with conc. HCl until pH=3-4. The solvent was removed under reduced pressure, the residue was triturated with H2O (3×10 mL) and ethyl acetate (3×10 mL) then dried to give 4-(3-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)phenethyl)benzoic acid (35 mg, 51%) as a yellow solid. 1H NMR (300 MHz, DMSO): δ 10.13 (s, 1H), 9.39 (s, 1H), 8.32-8.24 (m, 2H), 7.89-7.84 (m, 3H), 7.52-7.40 (m, 5H), 7.03 (d, 1H, J=8.7 Hz), 3.84 (s, 3H), 3.79 (s, 3H), 3.37 (brs, 4H). LC-MS: 513 [M+H]+, tR=1.67 min. HPLC: 97.30% at 214 nm, 97.09% at 254 nm, tR=5.16 min.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was triturated with H2O (3×10 mL) and ethyl acetate (3×10 mL)
  3. customthen dried

Sources & evidence

ORD record
ord-d75c984c96284185bf568aa8aabb565b
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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