6,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonate → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(6,6-dimethyl-cyclohex-1-en-1-yl)-phenyl]-methanone

HRID 1793981Notes

Reaction equation

HRID 1793981 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[C:44]([CH3:46])([CH3:45])[CH2:43][CH2:42][CH2:41][CH:40]=1)(=O)=O>C(OCC)C>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:43]4[C:44]([CH3:46])([CH3:45])[CH2:39][CH2:40][CH2:41][CH:42]=4)=[CH:19][C:18]=3[Cl:32])=[O:16])[CH2:6][C:5]=12

Participants

4

Reactant 2

HCID 106349276,6-Dimethyl-1-cyclohexen-1-yl trifluoromethanesulfonateHCID 22219716(10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

Product 1

HCID 10203011(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(6,6-dimethyl-cyclohex-1-en-1-yl)-phenyl]-methanoneYield 71.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 10, Step B (0.350 g, 0.780 mmol) and 6,6-dimethyl-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.222 g, 0.858 mmol) were reacted by the procedure described in Example 1, Step F. The crude product was purified by flash column chromatography on silica gel, eluting with 30% ethyl acetate in hexane to afford a clear oil. The oil was dissolved in diethyl ether and precipitated with petroleum ether to afford a white solid (0.240 g).

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with 30% ethyl acetate in hexane
  3. customto afford a clear oil
  4. customprecipitated with petroleum ether

Sources & evidence

ORD record
ord-4f2e486ca38545699bf1de7cd818b1a1
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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