2-(Thiophen-2-yl)benzoyl chloride → HCID 89593632, compound

HRID 2174977Notes

Reaction equation

HRID 2174977 reaction equation
[C:1]1([C:17]2C=C[CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([N:9]1[CH:16]2[CH:11]([CH2:12][CH2:13][NH:14][CH2:15]2)[CH2:10]1)=[O:8].C(OC(N1CCC2C(NC2)C1)=O)(C)(C)C.[S:38]1C=CC=C1C1C=CC=CC=1C(Cl)=O.C1(C2C=CC=CC=2)C(C(Cl)=O)=CC=CC=1>>[C@@H:16]12[N:9]([C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[C:17]3[S:38][CH:20]=[CH:19][CH:18]=3)=[O:8])[CH2:10][C@@H:11]1[CH2:12][CH2:13][NH:14][CH2:15]2

Participants

5

Reactant 4

HCID 27955572-(Thiophen-2-yl)benzoyl chlorideHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylateHCID 67086667HCID 67086667, compound

Product 1

HCID 89593632HCID 89593632, compoundYield 66.7%

Procedure

Intermediate 7 was prepared in a manner analogous to Intermediate 3, substituting (1R,6S) 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester for 3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester and 2-thiophen-2-yl-benzoyl chloride for biphenyl-2-carbonyl chloride in Step A. The final compound was concentrated and the residue was purified on HPLC to provide the title compound (150 mg, 66.7%). MS (ESI) mass calcd. for C17H18N2OS, 298.4; m/z found, 299.2. [M+H]+.

Workup

  1. concentrationThe final compound was concentrated
  2. customthe residue was purified on HPLC

Sources & evidence

ORD record
ord-d3cafa97afa446fe9bd4865fb627d0e3
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

Loading…