Triethylamine → N-(1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl)-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxamide

HRID 2425574Notes

Reaction equation

HRID 2425574 reaction equation
[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([CH:9]([NH2:11])C)[CH:5]=[N:4]1)[CH3:2].[F:12][C:13]([F:31])([F:30])[C:14]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27](O)=[O:28])[CH:23]=2)[N:18]=1)([CH3:16])[CH3:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH2:1]([N:3]1[C:7]([CH3:8])=[C:6]([CH2:9][NH:11][C:27]([C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([C:14]([CH3:16])([CH3:15])[C:13]([F:31])([F:30])[F:12])[CH:26]=[CH:25]3)=[O:28])[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 170246981-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethanamineHCID 574581632-(2,2,2-Trifluoro-1,1-dimethyl-ethyl)-quinoline-6-carboxylic acid

Product 1

HCID 59544178N-(1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)methyl)-2-(2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxamideYield 12.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (3 ml) solution of 1-(1-ethyl-5-methyl-1H-pyrazol-4-yl)ethanamine (95 mg, 0.62 mmol), (2,2,2-trifluoro-1,1-dimethylethyl)quinoline-6-carboxylic acid (176 mg, 0.62 mmol), HBTU (284 mg, 0.748 mmol) and triethylamine (0.434 ml, 3.12 mmol) were added and the mixture was stirred for 3 hours at room temperature. The reaction was quenched with sat. NaHCO3 aq and water, and the product was extracted with EtOAc/hexane (4:1) (3×20 ml). The combined organic extracts were dried over Na2SO4, and concentrated in vacuo. The crude material was purified by silica gel chromatography, using EtOAc/hexane (2:1) to give the title product (31 mg, 12%) as a white solid. 1H NMR (300 MHz, DMSO-d6) 1.27 (3H, t) 1.49 (3H, d), 1.71 (6H, s), 2.25 (3H, s), 4.01 (1H, q), 5.19 (1H, m), 7.44 (1H, s), 7.86 (1H, d), 8.06 (1H, d), 8.20 (1H, d), 8.51 (1H, d), 8.53 (1H, bs) 8.86 (1H, d). LCMS (ESI) RT=3.11 mins, m/z 417 (M−H)−, 419 (M+H)+.

Workup

  1. customThe reaction was quenched with sat. NaHCO3 aq and water
  2. extractionthe product was extracted with EtOAc/hexane (4:1) (3×20 ml)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-262cedfbe24d46369581b59defd851d0
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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