Triethylamine → HCID 90409365, compound

HRID 2177619Notes

Reaction equation

HRID 2177619 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[CH2:15][CH2:14][NH:13][CH:12]([CH3:17])[C:11]=3[N:10]=C2)=[N:6][CH:7]=1.[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].C[N:33](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[Cl:18][C:19]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:20]=1[C:21]([N:13]1[CH2:14][CH2:15][C:16]2[N:8]([C:5]3[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=3)[N:33]=[N:10][C:11]=2[CH:12]1[CH3:17])=[O:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 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 90409672HCID 90409672, compound

Product 1

HCID 90409365HCID 90409365, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(5-fluoropyrimidin-2-yl)-4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine (0.30 g, 1.28 mmol), 2-chloro-3-(trifluoromethyl)benzoic acid (0.34 g, 1.54 mmol), HATU (0.38 g, 1.28 mmol), and Et3N (0.18 mL, 1.28 mmol) in DMF (5 mL) was stirred for 30 min. The reaction was diluted with EtOAc (30 mL) and washed with H2O (3×20 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; MeOH(NH3):DCM) gave the title compound (0.51 g, 90%). 1H NMR (500 MHz, CDCl3) δ 8.80-8.43 (m, 2H), 7.82-7.44 (m, 1H), 7.27-7.15 (m, 2H), 6.66-6.60 (m, 1H), 5.95-4.92 (m, 1H), 3.77-2.54 (m, 3H), 1.74-1.53 (m, 3H). MS (ESI): mass calculated for C18H13ClF4N6O, 440.08. m/z found, 441.0 [M+H]+.

Workup

  1. washwashed with H2O (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-36ac3943487d48e6948c7f9b82570b69
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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