Acetic Acid → HCID 178475923, compound

HRID 2282205Notes

Reaction equation

HRID 2282205 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][NH2:26].[C:27]([OH:30])(=[O:29])[CH3:28]>COC(OC)(N(C)C)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][C:27]([CH3:28])=[N:26][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 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 66854680HCID 66854680, compound

Product 1

HCID 178475923HCID 178475923, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 878351,1-Dimethoxyethyl(dimethyl)amineSolvent

Conditions

Temperature
90 °C

Procedure

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 same manner as in Example 35-B(ix) was suspended in N,N-dimethylacetamide dimethyl acetal (2 mL), and the mixture 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 (72 mg, 70%) 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-58674f0029e4454a908f5b6be0822914
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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