Diisopropylethylamine → (R)-4-(4-oxo-4,5-dihydro-thiazolo[4,5-d]pyridazin-2-yl)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

HRID 908642Notes

Reaction equation

HRID 908642 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:32]=[CH:31][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]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:6][CH:5]=1.Cl[C:36]1[S:37][C:38]2[CH:43]=[N:42][NH:41][C:40](=[O:44])[C:39]=2[N:45]=1.C(N(CC)C(C)C)(C)C>C(O)(C)C>[F:34][C:2]([F:1])([F:33])[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:36]3[S:37][C:38]4[CH:43]=[N:42][NH:41][C:40](=[O:44])[C:39]=4[N:45]=3)[CH2:15][CH2:14][N:13]2[S:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[O:11])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 597037792-chloro-5H-thiazolo[4,5-d]pyridazin-4-oneHCID 59703788(R)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamide

Product 1

HCID 59703772(R)-4-(4-oxo-4,5-dihydro-thiazolo[4,5-d]pyridazin-2-yl)-1-(4-trifluoromethyl-benzenesulfonyl)-piperazine-2-carboxylic acid 4-trifluoromethoxy-benzylamideYield 74.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of the compound (87 mg) obtained in Example 983, Step 2 and the compound (32 mg) obtained in Step 5 in isopropanol (0.9 ml) was added N,N-diisopropylethylamine (30 μl) at room temperature. After stirring overnight at room temperature, and the mixture was stirred with heating under reflux for 5 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by thin layer silica gel chromatography (methanol:chloroform=5:95) to give the title compound (84 mg).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating
  3. temperatureunder reflux for 5 hr
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by thin layer silica gel chromatography (methanol:chloroform=5:95)

Sources & evidence

ORD record
ord-1b62d695dc8e4829bef6f5b34547bec1
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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