1,2-Dichloroethane → HCID 67339376, compound

HRID 1909145Notes

Reaction equation

HRID 1909145 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=O.[O-:18][N+:19]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[C:21]([C@H:29]([NH2:31])[CH3:30])[CH:20]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([NH:31][C@@H:29]([C:21]1[CH:20]=[N+:19]([O-:18])[C:24]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:22]=1)[CH3:30])=[O:16]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 247297975-(2,4-Difluorophenyl)pyridine-3-carboxylic acidHCID 59539683(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine

Product 1

HCID 67339376HCID 67339376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2,4-difluorophenyl)nicotinic acid (40.0 mg, 0.15 mmol) in DMF (0.7 mL) were added hydrochloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (49.3 mg, 0.18 mmol), EDC (33.9 mg, 0.18 mmol), HOBT (22.6 mg, 0.15 mmol) and triethylamine (0.10 mL, 0.74 mmol). The mixture was stirred at ambient temperature for 18 h. Purification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title product, which was converted to hydrochloride salt using 2.0 M HCl in ether (47 mg). HRMS 424.1086. 1H NMR (400 MHz, CD3OD): δ 9.22 (s, 1H); 9.15 (s, 1H); 9.00 (s, 1H); 8.52 (s, 1H); 7.92 (d, J=8.4 Hz, 1H); 7.83-7.73 (m, 1H); 7.70 (d, J=8.4 Hz, 1H); 7.31-7.21 (m, 2H); 5.33-5.25 (m, 1H); 1.67 (d, J=7.1 Hz, 3H).

Workup

  1. customPurification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6cf30071fbd14681843e7063e66262a2
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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