Diisopropylethylamine → HCID 57703904, compound

HRID 1472211Notes

Reaction equation

HRID 1472211 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.Cl.[CH2:15]([O:17][C:18]([N:20]1[C:24]([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[N+:40]([O-:42])=[O:41])=[C:23]2[CH2:44][NH:45][C:46]([CH3:48])([CH3:47])[C:22]2=[N:21]1)=[O:19])[CH3:16].C(N(CC)C(C)C)(C)C>ClCCl>[CH2:15]([O:17][C:18]([N:20]1[C:24]([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[CH:29][C:28]=2[N+:40]([O-:42])=[O:41])=[C:23]2[CH2:44][N:45]([S:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)(=[O:11])=[O:10])[C:46]([CH3:47])([CH3:48])[C:22]2=[N:21]1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27740583,5-Difluorobenzenesulfonyl chlorideHCID 67009100HCID 67009100, compound

Product 1

HCID 57703904HCID 57703904, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-difluoro-benzenesulfonyl chloride (1 eq., 3.9 g, 18.4 mmol) was added portion-wise to a stirred solution of 6,6-dimethyl-3-[4-(4-methyl-piperazin-1-yl)-2-nitro-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-2-carboxylic acid ethyl ester dihydrochloride (10 g, 18.4 mmol) and N,N-diisopropylethylamine (6 eq, 19.3 mL, 110.4 mmol) in dry dichloromethane (100 mL) at room temperature. Stirring was continued for about 4 hours. The reaction mixture was diluted with dichloromethane (100 mL) then washed with saturated sodium hydrogen carbonate (150 mL), dried over sodium sulphate, evaporated to dryness and purified by flesh chromatography on silica gel using acetone as the eluant. The title compound was obtained as yellow solid (9 g, 65% yield).

Workup

  1. washthen washed with saturated sodium hydrogen carbonate (150 mL)
  2. dry with materialdried over sodium sulphate
  3. customevaporated to dryness
  4. custompurified by flesh chromatography on silica gel

Sources & evidence

ORD record
ord-308e10cf5a01449788f2519a3f88a165
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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