Methanesulfonyl chloride → HCID 86722364, compound

HRID 718776Notes

Reaction equation

HRID 718776 reaction equation
[CH2:1]([O:8][C@@:9]1([C:36]([F:39])([F:38])[F:37])[CH2:33][C@H:13]2[CH2:14][CH2:15][CH2:16][C:17]3[C:18](=[CH:19][C:20]4[CH:21]=[N:22][N:23]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)[C:24]=4[CH:25]=3)[C@:12]2([CH2:34][NH2:35])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH2:1]([O:8][C@@:9]1([C:36]([F:38])([F:39])[F:37])[CH2:33][C@H:13]2[CH2:14][CH2:15][CH2:16][C:17]3[C:18](=[CH:19][C:20]4[CH:21]=[N:22][N:23]([C:26]5[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=5)[C:24]=4[CH:25]=3)[C@:12]2([CH2:34][NH:35][S:41]([CH3:40])(=[O:43])=[O:42])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86722363HCID 86722363, compound

Product 1

HCID 86722364HCID 86722364, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Crude ((3R,4aR,12bS)-3-(benzyloxy)-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-12b-yl)methan amine (34, R1=4-Fluorophenyl, R3=Trifluoromethyl, R4═H, R3=Benzyl) (0.135 mmol) was dissolved in DCM (3 mL) and methanesulfonyl chloride (0.026 mL, 0.334 mmol) and TEA (0.023 mL, 0.167 mmol) were added at rt. The reaction was stirred at rt for about 30 min, then diluted with DCM (10 mL) and concentrated with silica gel (3 g). The residue was purified on silica gel using a gradient of 0-10% EtOAc in DCM. Product fractions were combined and concentrated to yield N-(((3R,4aR,12bS)-3-(benzyloxy)-9-(4-fluorophenyl)-3-(trifluoromethyl)-1,2,3,4,4a,5,6,7,9,12b-decahydrobenzo[6,7]cyclohepta[1,2-f]indazol-12b-yl)methyl)methanesulfonamide (35, R1=4-Fluorophenyl, R3=Trifluoromethyl, R4=Methanesulfonyl, R3=Benzyl) (40 mg, 39%) as a clear glass; LC/MS, method 3, Rt=2.95 min, MS m/z 616 (M+H)+.) The residue was used in step #4 without further purification.

Workup

  1. concentrationconcentrated with silica gel (3 g)
  2. customThe residue was purified on silica gel using a gradient of 0-10% EtOAc in DCM
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3b71d697b5864a8c991e8eb98ec9f108
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

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