Acetic Acid → HCID 178475923, compound

HRID 1530043Notes

Reaction equation

HRID 1530043 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-a987e4d36ccb462ca5ef17b039fca62f
Source dataset
uspto-grants-2015_07
Patent number
US09090601B2

Reaction notes

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