1,2-Dichloroethane → HCID 90041838, compound

HRID 530406Notes

Reaction equation

HRID 530406 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([OH:27])=O)[CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[CH:7]=1.[CH3:28][S:29]([NH2:32])(=[O:31])=[O:30].C(Cl)CCl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([NH:32][S:29]([CH3:28])(=[O:31])=[O:30])=[O:27])[CH:20]=2)[CH:5]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([C:15]([F:16])([F:17])[F:18])[CH:12]=[CH:11][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 72879MethanesulfonamideHCID 73297228HCID 73297228, compound

Product 1

HCID 90041838HCID 90041838, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A cloudy solution of 3′-methyl-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-3-carboxylic acid (100 mg, 0.222 mmol), methanesulfonamide (24.3 mg, 0.256 mmol), DMAP (5.4 mg, 0.044 mmol), EDC (59.7 mg, 0.311 mmol), and triethylamine (0.043 mL, 0.31 mmol) in DMF (4 mL) was stirred for 14 hours at room temperature. The reaction mixture was purified directly via reverse phase HPLC (CH3CN:H2O with 0.1% TFA) to give 3′-methyl-N-(methylsulfonyl)-5′-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}biphenyl-3-carboxamide. MS ESI calc'd. for C20H18F3N4O3S [M+H]+ 451, found 451. 1H NMR (500 MHz, DMSO-d6) δ 12.26 (s, 1H), 10.26 (s, 1H), 8.82 (d, J=4.9 Hz, 1H), 8.18 (s, 1H), 7.95 (s, 1H), 7.90 (d, J=7.8 Hz, 1H), 7.87 (d, J=7.9 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.57 (s, 1H), 7.26 (d, J=5.0 Hz, 1H), 7.24 (s, 1H), 3.39 (s, 3H), 2.38 (s, 3H).

Workup

  1. customThe reaction mixture was purified directly via reverse phase HPLC (CH3CN:H2O with 0.1% TFA)

Sources & evidence

ORD record
ord-e3ce8087cf5340a8b68c2a2eba385655
Source dataset
uspto-grants-2016_05
Patent number
US09353066B2

Reaction notes

Loading…