Isopropanol → (R)-4-(7-oxo-6,7-dihydrothiazolo[4,5-d]pyridazin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908635Notes

Reaction equation

HRID 908635 reaction equation
[F:1][C:2]([F:35])([F:34])[O:3][C:4]1[CH:33]=[CH:32][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][NH:16][CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:31])([F:30])[F:29])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Cl[C:37]1[S:38][C:39]2[C:44](=[O:45])[NH:43][N:42]=[CH:41][C:40]=2[N:46]=1.C(O)(C)C>C(N(CC)CC)C>[F:35][C:2]([F:1])([F:34])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:37]3[S:38][C:39]4[C:44](=[O:45])[NH:43][N:42]=[CH:41][C:40]=4[N:46]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([O:27][C:28]([F:29])([F:30])[F:31])=[CH:23][CH:22]=2)(=[O:19])=[O:20])=[O:11])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 597037132-chloro-6H-thiazolo[4,5-d]pyridazin-7-oneHCID 59703800(R)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

Product 1

HCID 59703755(R)-4-(7-oxo-6,7-dihydrothiazolo[4,5-d]pyridazin-2-yl)-1-(4-trifluoromethoxy-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixed solution of the compound (26 mg) obtained in Example 783, the compound (10 mg) obtained in Step 6 and isopropanol (1.0 ml) was added triethylamine (14 μl) at room temperature, and the mixture was heated under reflux overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (methanol:chloroform=1:20, developed twice) to give the title compound (31 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by thin layer silica gel chromatography (methanol

Sources & evidence

ORD record
ord-59236c2e876944b590d91a9b414dcfc8
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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