Methanesulfonic acid, trifluoro-, 2-methyl-3-oxo-1-cyclohexen-1-yl ester → 3-[2-Chloro-5-methoxy-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl-carbonyl)phenyl]-2-methyl-cyclohex-2-en-1-one

HRID 1793978Notes

Reaction equation

HRID 1793978 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]=[C:21]([Cl:23])[C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][C:18]=3[O:33][CH3:34])=[O:16])[CH2:6][C:5]=12.FC(F)(F)S([O:40][C:41]1[CH2:46][CH2:45][CH2:44][C:43](=O)[C:42]=1[CH3:48])(=O)=O>>[Cl:23][C:21]1[CH:22]=[C:17]([C:15]([N:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH2:10][N:4]3[CH:3]=[CH:2][CH:1]=[C:5]3[CH2:6]2)=[O:16])[C:18]([O:33][CH3:34])=[CH:19][C:20]=1[C:43]1[CH2:44][CH2:45][CH2:46][C:41](=[O:40])[C:42]=1[CH3:48]

Participants

3

Reactant 2

HCID 10825071Methanesulfonic acid, trifluoro-, 2-methyl-3-oxo-1-cyclohexen-1-yl esterHCID 22219703[10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl][5-chloro-2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone

Product 1

HCID 102048863-[2-Chloro-5-methoxy-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl-carbonyl)phenyl]-2-methyl-cyclohex-2-en-1-oneYield 40.1%

Procedure

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[5-chloro-2-methoxy-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 1, Step E (0.700 g, 1.46 mmol) and 2-methyl-3-oxo-cyclohex-1-en-1-yl trifluoromethanesulfonate (0.416 g, 1.61 mmol) were reacted by the procedure described in Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with 50% ethyl acetate in hexane followed by precipitation from diethyl ether with pentane afforded the title compound (0.270 g) as an amorphous yellow solid.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with 50% ethyl acetate in hexane
  3. customfollowed by precipitation from diethyl ether with pentane

Sources & evidence

ORD record
ord-9ffdfa35beab433fb20a128fc7e91121
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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