Triethylamine → HCID 25196490, compound

HRID 241569Notes

Reaction equation

HRID 241569 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH:15]C(=O)OC(C)(C)C)[CH2:13][C@@H:12]([N:23]2[CH2:30][C:29]3[CH:28]=[N:27][NH:26][C:25]=3[CH2:24]2)[C:11](=O)[N:10]1[CH3:32].C(N(CC)CC)C.[CH:40]1([S:43](Cl)(=[O:45])=[O:44])[CH2:42][CH2:41]1.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48].C(Cl)Cl>ClCCl>[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[F:50][C:49]([F:52])([F:51])[C:47]([OH:53])=[O:48].[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@H:9]1[C@@H:14]([NH2:15])[CH2:13][C@@H:12]([N:23]2[CH2:30][C:29]3[C:25](=[N:26][N:27]([S:43]([CH:40]4[CH2:42][CH2:41]4)(=[O:45])=[O:44])[CH:28]=3)[CH2:24]2)[CH2:11][N:10]1[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2760919Cyclopropanesulfonyl chlorideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86657486HCID 86657486, compound

Product 1

HCID 25196490HCID 25196490, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl [(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydropyrrolo[3,4-c]pyrazol-5(1H)-yl)-1-methyl-6-oxopiperidin-3-yl]carbamate (70 mg, 0.161 mmol) in dichloromethane (4 mL) at room temperature, triethylamine (0.068 mL, 0.484 mmol) and cyclopropanesulfonyl chloride (0.037 mL, 0.363 mmol) were added. The mixture was stirred for 4 days at room temperature. The residue was purified by preparative TLC on silica gel, eluting with CH2Cl2/MeOH/aqueous NH3 (95/4/1) to give first eluting isomer as isomer A and second eluting isomer as isomer B. Isomer A was treated with TFA/CH2Cl2=1:1 for 1 h to give the title compound. LC-MS: 437.89 (M+1).

Workup

  1. customThe residue was purified by preparative TLC on silica gel
  2. washeluting with CH2Cl2/MeOH/aqueous NH3 (95/4/1)
  3. customto give first eluting isomer as isomer A and second eluting isomer as isomer B

Sources & evidence

ORD record
ord-cad38299e1c3464cb742303252a9b9be
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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