Ethyl Acetate → HCID 66854895, compound

HRID 2282206Notes

Reaction equation

HRID 2282206 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.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH3:1][C:2]1[C:9]([C:10]2[S:11][C:12]([C:21]#[N:23])=[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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66854680HCID 66854680, compound

Product 1

HCID 66854895HCID 66854895, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(6-methylpyrazolo[5,1-b][1,3]thiazol-7-yl)-4-phenyl-1,3-thiazole-5-carboxamide (270 mg, 0.80 mmol) produced in the same manner as in Example 35-B (ix) in tetrahydrofuran (20 mL) was added Burgess reagent (230 mg, 0.96 mmol), and the mixture was stirred for 30 min. The reaction solution was added to ethyl acetate (100 mL) and saturated aqueous sodium bicarbonate solution (100 mL). The resulting solid was collected by filtration, washed with water and dried to give the title compound (110 mg, 42%) as a colorless solid.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-ef0dd9b6ba4c4b1182662ffc31d9c81c
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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