Triethylamine → HCID 15896224, compound

HRID 2355813Notes

Reaction equation

HRID 2355813 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([Br:13])=[CH:11][N:10]([CH3:14])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[F:22][C:23]([F:36])([F:35])[O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32](O)=[O:33])=[CH:27][CH:26]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Br:13][C:12]1[C:8]([C:4]2[CH:3]=[C:2]([NH:1][C:32](=[O:33])[CH2:31][C:28]3[CH:29]=[CH:30][C:25]([O:24][C:23]([F:35])([F:22])[F:36])=[CH:26][CH:27]=3)[CH:7]=[CH:6][CH:5]=2)=[N:9][N:10]([CH3:14])[CH:11]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27353913-(4-Bromo-1-Methyl-1H-Pyrazol-3-Yl)AnilineHCID 27773192-[4-(Trifluoromethoxy)phenyl]acetic acid

Product 1

HCID 15896224HCID 15896224, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 3-(3-aminophenyl)-4-bromo-1-methylpyrazole (35 mg, 0.14 mmol) and triethylamine (23 μL, 0.17 mmol) in DMF (0.5 mL) was added in one portion to a stirred solution of 4-trifluoromethoxyphenylacetic acid (31 mg, 0.14 mmol), HBTU (53 mg, 0.14 mmol) and HOBT (19 mg, 0.14 mmol) in DMF (1 mL). The mixture was heated at 70° C. for 24 h and then quenched with aqueous sodium bicarbonate solution. Ethyl acetate was added and the organic phase separated, washed with water (.times.3), brine, dried (MgSO4) and evaporated. Chromatography on flash silica (50% EtOAc/hexane) gave the title compound as a colourless solid (43 mg, 68%). m.p. 141.2-142.5° C. (EtOAc/hexane).

Workup

  1. customquenched with aqueous sodium bicarbonate solution
  2. additionEthyl acetate was added
  3. customthe organic phase separated
  4. washwashed with water (.times.3), brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-e45efc1c888e48ff9df37c3a6e345619
Source dataset
uspto-grants-2010_07
Patent number
US07754866B2

Reaction notes

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