Acetic Acid → HCID 178475920, compound

HRID 1530042Notes

Reaction equation

HRID 1530042 reaction equation
[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]([NH2:23])=O)=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1.O.[NH2:25]N.[C:27]([OH:30])(=[O:29])[CH3:28].COC(OC)[N:34]([CH3:36])C>>[C:27]([OH:30])(=[O:29])[CH3:28].[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]3[NH:23][CH:36]=[N:34][N:25]=3)=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[C:5]2[S:6][CH:7]=[CH:8][N:4]2[N:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 66854680HCID 66854680, compound

Product 1

HCID 178475920HCID 178475920, compoundYield 33%

Conditions

Temperature
90 °C

Procedure

A suspension of 2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazole-5-carboxamide (79 mg, about 0.23 mmol) produced in the above in N,N-dimethylformamide dimethyl acetal (2 mL) was stirred at 90° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, hydrazine monohydrate (0.017 mL, 0.35 mmol) and acetic acid (2 mL) were added to the residue, and the mixture was stirred at 90° C. for 1 hr. The reaction mixture was cooled to room temperature, and the resulting solid was collected by filtration and washed with ethyl acetate to give the title compound (27.8 mg, 33%) as a white solid.

Workup

  1. additionwere added to the residue
  2. stirringthe mixture was stirred at 90° C. for 1 hr
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-e59a08dd3f5049e8977a878132b299db
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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