1,2-Dichloroethane → HCID 25152660, compound

HRID 1665788Notes

Reaction equation

HRID 1665788 reaction equation
[F:1][C:2]1([F:33])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:32])=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([C:29](O)=[O:30])[CH:24]=5)[CH:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1.[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].C(Cl)CCl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:33][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([C:11]3([C:14]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([CH3:32])=[C:21]([C:23]5[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:38][S:35]([CH3:34])(=[O:37])=[O:36])=[O:30])[CH:24]=5)[CH:22]=4)=[O:15])[CH2:13][CH2:12]3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 72879MethanesulfonamideHCID 59205949HCID 59205949, compound

Product 1

HCID 25152660HCID 25152660, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5′-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2′-methylbiphenyl-3-carboxylic acid (50 mg, 0.11 mmol), methansulfonamide (7.0 mg, 0.074 mmol), DMAP (13 mg, 0.11 mmol), and CH2Cl2 (1 mL) was added EDC (28 mg, 0.15 mmol) at ambient temperature. The mixture was allowed to stir for 18 h before it was concentrated. The residue was taken up in DMF (1 mL) and was purified by reverse phase preparatory HPLC to provide 5′-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-2′-methyl-N-(methylsulfonyl)biphenyl-3-carboxamide as a white solid. ESI-MS m/z calc. 528.5, found 529.2 (M+1)+. Retention time 1.97 minutes.

Workup

  1. concentrationwas concentrated
  2. customwas purified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-80cb509e5acd42a5b6775cc557bc1012
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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