Methanesulfonyl chloride → HCID 86598337, compound

HRID 1270416Notes

Reaction equation

HRID 1270416 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[CH2:31][C@H:32](O)[CH2:33][C@H:17]3[CH2:16]2)=[O:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:37]([N:40](C(C)C)[CH2:41][CH3:42])(C)[CH3:38].CS(Cl)(=O)=[O:48]>C(OCC)(=O)C>[F:12][C:9]([F:11])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([N:15]2[C@H:20]([CH2:21][C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)[CH2:19][N:18]3[CH2:31][C@@H:32]([N:40]4[CH2:41][CH2:42][O:48][CH2:38][CH2:37]4)[CH2:33][C@H:17]3[CH2:16]2)=[O:14])[CH:4]=[C:3]([C:2]([F:35])([F:1])[F:36])[CH:8]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86598338HCID 86598338, compound

Product 1

HCID 86598337HCID 86598337, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3,5-bis(trifluoromethyl)phenyl-[(3R,7R,8aS)-7-hydroxy-3-(1H-indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazin-2-yl]-methanone (0.54 g) in ethyl acetate (20 mL) was added diisopropylethylamine (2 mL) and methanesulfonyl chloride (0.2 mL). The resulting mixture was stirred overnight at room temperature and concentrated in vacuo. To the residue was added morpholine (4 mL) and the mixture was heated at 95° C. for 4 hours. The excess morpholine was removed in vacuo and the residue purified by preparative HPLC to afford 3,5-bis(trifluoromethyl)phenyl-[(3R,7S,8aS)-3-(1H-indol-3-ylmethyl)-7-(morpholin-4-yl)-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl]-methanone (81 mg). MH+ 581 (compound 6).

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added morpholine (4 mL)
  3. temperaturethe mixture was heated at 95° C. for 4 hours
  4. customThe excess morpholine was removed in vacuo
  5. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-3647843f73824a4eac47a6e6e7f3eb8d
Source dataset
uspto-grants-2007_04
Patent number
US07202238B2

Reaction notes

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