Acetyl chloride → HCID 178489147, compound

HRID 1452757Notes

Reaction equation

HRID 1452757 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH2:17])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1.[C:18](Cl)(=[O:20])[CH3:19].C(O)C(N)(CO)CO>CN(C1C=CN=CC=1)C.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]3[S:15][C:14]([NH:17][C:18](=[O:20])[CH3:19])=[N:13][C:12]=3[NH:11][N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 178489152HCID 178489152, compound

Product 1

HCID 178489147HCID 178489147, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a vial charged with 3-(4-methoxyphenyl)-1H-pyrazolo[3,4-d]thiazol-5-ylamine (100 mg, 0.306 mmol), PS-DMAP (Argonaut resin, 1.2 g, 6 equiv.), and a stirring bar was added THF (3 mL) and acetyl chloride (110 μL, 1.53 mmol). The reaction mixture was stirred at 70° C. for 1 hour, then cooled to room temperature and treated with PS-trisamine (Argonaut resin, 1.1 g, 20 equiv.) for 1 hour. The resin was filtered, washed with THF and the solvent was evaporated. The resulting crude was suspended in MeOH and treated with hydrazine monohydrate (0.06 mL) for 30 minutes. The precipitate was filtered, and the filtrate was directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent to provide 12.5 mg (14% yield) of N-[3-(4-methoxy-phenyl)-1H-pyrazolo[3,4-d]thiazol-5-yl]-acetamide as an off-white solid. 1H-NMR (d6-DMSO) δ: 13.4 (broad s, 1H), 12.3 (broad s, 1H), 7.66 (broad s, 2H), 7.09 (broad s, 2H), 3.80 (s, 3H), 2.18 (s, 3H); HPLC/MS m/z: 289.0 [MH]+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationThe resin was filtered
  3. washwashed with THF
  4. customthe solvent was evaporated
  5. additiontreated with hydrazine monohydrate (0.06 mL) for 30 minutes
  6. filtrationThe precipitate was filtered
  7. customthe filtrate was directly purified on silica gel with 0-10% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-37f66ed7e7284a59ac3cc9dcafeed0f2
Source dataset
uspto-grants-2009_01
Patent number
US07473783B2

Reaction notes

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