HCID 57703895, compound → HCID 24751332, compound

HRID 1472215Notes

Reaction equation

HRID 1472215 reaction equation
C(OC([N:6]1[C:10]2[CH2:11][N:12]([S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)(=[O:16])=[O:15])[CH2:13][C:9]=2[C:8]([NH:24][C:25](=[O:45])[C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]3)=[C:28]([N:39]([CH2:41][CH2:42][O:43]C)[CH3:40])[CH:27]=2)=[N:7]1)=O)C>B(Br)(Br)Br.ClCCl>[F:23][C:19]1[CH:18]=[C:17]([S:14]([N:12]2[CH2:13][C:9]3[C:8]([NH:24][C:25](=[O:45])[C:26]4[CH:31]=[CH:30][C:29]([N:32]5[CH2:33][CH2:34][N:35]([CH3:38])[CH2:36][CH2:37]5)=[C:28]([N:39]([CH2:41][CH2:42][OH:43])[CH3:40])[CH:27]=4)=[N:7][NH:6][C:10]=3[CH2:11]2)(=[O:15])=[O:16])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 57703895HCID 57703895, compound

Product 1

HCID 24751332HCID 24751332, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Procedure

A solution of 5-(3-fluoro-benzenesulfonyl)-3-[3-[(2-methoxy-ethyl)-methyl-amino]-4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester (120 mg, 0.186 mmol) in 5 mL of 1M BBr3 in dichloromethane was stirred at room temperature for 24 h. The mixture was washed with saturated aqueous NaHCO3 and the combined organic layers were evaporated to dryness. The resulting crude (110 mg) was then dissolved in 4 mL of MeOH and 0.5 mL of triethylamine and the mixture was stirred at room temperature for 3 h. The solvent was removed and the final product was purified by flash column chromatography, using dichloromethane-methanol-aqueous ammonia 9:1:0.5 as eluant, affording 70 mg of yellow solid.

Workup

  1. washThe mixture was washed with saturated aqueous NaHCO3
  2. customthe combined organic layers were evaporated to dryness
  3. dissolutionThe resulting crude (110 mg) was then dissolved in 4 mL of MeOH
  4. customThe solvent was removed
  5. customthe final product was purified by flash column chromatography

Sources & evidence

ORD record
ord-dcc6b91e6c844c0b92ce1d042985eb23
Source dataset
uspto-grants-2015_04
Patent number
US09012487B2

Reaction notes

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