Diethyl Ether → HCID 11190290, compound

HRID 859199Notes

Reaction equation

HRID 859199 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[N:12]=[C:11]([C:21](O)=[O:22])[C:10]=2[O:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:5][CH:4]=1.C(N(CC)CC)C.C(OCC)C>ClCCCl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[N:12]=[C:11]3[C:10]=2[O:24][CH2:25][CH2:26][N:27]([CH2:28][C:29]([F:30])([F:32])[F:31])[C:21]3=[O:22])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 131726168HCID 131726168, compound

Product 1

HCID 11190290HCID 11190290, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 5-(4-chlorophenyl)-1-(2-chlorophenyl)-4-[2-(2,2,2-trifluoroethylamino)-ethoxy]-1H-pyrazole-3-carboxylic acid, hydrochloride I-1h (45 mg, 0.1 mmol), triethylamine (0.05 ml) and 1-propanephosphoric acid cyclic anhydride (0.1 ml, 0.14 mmol) in 1,2-dichloroethane (0.6 ml) were stirred for 8 hours. The reaction was diluted into ethyl ether, washed 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine, dried (Na2SO4) and concentrated in vacuo to afford the title compound (1A-1) as a white solid, 35 mg. 1H NMR in CDCl3 (ppm): δ7.52 (d, 1H), 7.38–7.34 (m, 2H), 7.23 (d, 2H), 7.15 (d, 2H), 4.47 (brs, 2H), 4.29 (br s, 2H), 3.91 (br s, 2H); ms (LCMS) m/z=456.3 (M+1).

Workup

  1. washwashed 1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9dac3d61b7064bbcae70d7f98c7a77e1
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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