Triethylamine → HCID 25196492, compound

HRID 241568Notes

Reaction equation

HRID 241568 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.[F:40][C:41]([F:47])([F:46])[S:42](Cl)(=[O:44])=[O:43].[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49].C(Cl)Cl>ClCCl>[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[F:51][C:50]([F:53])([F:52])[C:48]([OH:54])=[O:49].[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:42]([C:41]([F:47])([F:46])[F:40])(=[O:44])=[O:43])[CH:28]=3)[CH2:24]2)[CH2:11][N:10]1[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86657486HCID 86657486, compound

Product 1

HCID 25196492HCID 25196492, 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 (60 mg, 0.138 mmol) in dichloromethane (4 mL) at room temperature, triethylamine (0.048 mL, 0.346 mmol) and trifluoromethanesulfonyl chloride (0.029 mL, 0.277 mmol) were added. The mixture was stirred overnight 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 1:1 TFA/CH2Cl2 for 1 h to give the title compound. LC-MS: 465.84 (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-c83fc083a5a945bc8954168edb4cbb41
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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