Triethylamine → HCID 25196150, compound

HRID 241567Notes

Reaction equation

HRID 241567 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.[CH3:40][S:41](Cl)(=[O:43])=[O:42].[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46].C(Cl)Cl>ClCCl>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[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:41]([CH3:40])(=[O:43])=[O:42])[CH:28]=3)[CH2:24]2)[CH2:11][N:10]1[CH3:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86657486HCID 86657486, compound

Product 1

HCID 25196150HCID 25196150, 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 (55.5 mg, 0.128 mmol) in dichloromethane (5 mL) at room temperature, triethylamine (0.045 mL, 0.320 mmol) and methanesulfonyl chloride (0.011 mL, 0.147 mmol) were added. The mixture was stirred for 1 h at room temperature. The residue was purified by prep TLC on silica gel, eluting with EtOAc/MeOH/NH4OH (90/9/1) 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: 411.92 (M+1).

Workup

  1. customThe residue was purified by prep TLC on silica gel
  2. washeluting with EtOAc/MeOH/NH4OH (90/9/1)
  3. customto give first eluting isomer as isomer A and second eluting isomer as isomer B

Sources & evidence

ORD record
ord-d54b8477714e4fc6b23b5412cb3022d9
Source dataset
uspto-grants-2014_02
Patent number
US08653059B2

Reaction notes

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