Hydrazine → HCID 178456807, compound

HRID 1671795Notes

Reaction equation

HRID 1671795 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([C:14]1[CH:26]=[CH:25][C:17]2[N:18]=[C:19]([NH:21][CH:22]([CH3:24])[CH3:23])[S:20][C:16]=2[CH:15]=1)[C:10]([O:12]C)=O.[NH2:28][NH2:29].[OH-].[NH4+].CO.C(Cl)Cl>CC(O)=O.CCO.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([C:14]2[CH:26]=[CH:25][C:17]3[N:18]=[C:19]([NH:21][CH:22]([CH3:23])[CH3:24])[S:20][C:16]=3[CH:15]=2)=[C:10]([OH:12])[NH:29][N:28]=1

Participants

8

Reactant 4

HCID 9321HydrazineHCID 14923Ammonium HydroxideHCID 21226129Dichloromethane methanolHCID 57527151Methyl 3-(2-fluorophenyl)-2-(2-(isopropylamino)benzo[d]thiazol-6-yl)-3-oxopropanoate

Product 1

HCID 178456807HCID 178456807, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of methyl 3-(2-fluorophenyl)-2-(2-(isopropylamino)benzo[d]thiazol-6-yl)-3-oxopropanoate(63% purity, 0.260 g) in glacial AcOH (4 mL) and EtOH (2 mL) was added anhydrous hydrazine (0.18 mL, 5.73 mmol) at 0° C. The resulting mixture was heated at 85° C. for 4 hr. After it cooled to rt, the mixture was diluted with water (40 mL), basified with concentrated ammonium hydroxide to pH 8, and extracted with AcOEt (3×30 mL). The combined extract was washed with brine and dried over anhydrous MgSO4. The title compound (55.0 mg, 27% yield over two steps) was isolated by ISCO (8% MeOH/CH2Cl2). (M+H)+=369.21.

Workup

  1. temperatureAfter it cooled to rt
  2. extractionextracted with AcOEt (3×30 mL)
  3. extractionThe combined extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous MgSO4

Sources & evidence

ORD record
ord-d37f9aed406d4ca99b34109e48de668e
Source dataset
uspto-grants-2011_08
Patent number
US07994337B2

Reaction notes

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