Diisopropylethylamine → HCID 86270721, compound

HRID 2177574Notes

Reaction equation

HRID 2177574 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[CH:4]1[C:9]2[N:10]=[CH:11][NH:12][C:8]=2[CH2:7][CH2:6][NH:5]1.[Cl:15][C:16]1[C:24]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:15][C:16]1[C:24]([C:25]([F:27])([F:28])[F:26])=[CH:23][CH:22]=[CH:21][C:17]=1[C:18]([N:5]1[CH2:6][CH2:7][C:8]2[NH:12][CH:11]=[N:10][C:9]=2[CH:4]1[C:3]([F:2])([F:13])[F:14])=[O:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27366772-Chloro-3-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90410566HCID 90410566, compound

Product 1

HCID 86270721HCID 86270721, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine hydrochloride (0.10 g, 0.44 mmol), 2-chloro-3-trifluoromethyl benzoic acid (0.10 g, 0.44 mmol), HATU (0.18 g, 0.48 mmol, and DIPEA (0.19 mL, 1.1 mmol) in DMF (2 mL) was stirred for 30 min. The reaction was diluted with EtOAc (15 mL) and washed with H2O (3×10 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.06 g, 34%). 1H NMR (500 MHz, CDCl3) δ 8.02-7.94 (m, 1H), 7.80-7.58 (m, 1H), 7.51-7.39 (m, 1H), 6.60-6.50 (m, 1H), 4.42 (q, J=7.6 Hz, 1H), 2.95 (s, 4H). MS (ESI): mass calculated for C15H10ClF6N3O, 397.042. m/z found 398.1 [M+H]+.

Workup

  1. washwashed with H2O (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ad075f7e3ddb454cafae64570edfaf1a
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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