Triethylamine → HCID 69101849, compound

HRID 1809155Notes

Reaction equation

HRID 1809155 reaction equation
N1N=CN([C:6]2[CH:7]=[C:8](C=CC=2)[O:9][CH2:10][C:11](O)=[O:12])C=1.C1C=CC2N(O)[N:24]=[N:23]C=2C=1.CCN=C=N[CH2:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].C(N(CC)CC)C.[NH2:45][C:46]1[CH:47]=[CH:48][C:49]([Cl:56])=[C:50]([C:52]([F:55])([F:54])[F:53])[CH:51]=1>CN(C=O)C>[Cl:56][C:49]1[CH:48]=[CH:47][C:46]([NH:45][C:11](=[O:12])[CH2:10][O:9][C:8]2[CH:32]=[CH:33][C:34]([N:35]3[CH2:36][NH:24][N:23]=[CH:37]3)=[CH:6][CH:7]=2)=[CH:51][C:50]=1[C:52]([F:53])([F:54])[F:55]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 757711-HydroxybenzotriazoleHCID 26316549HCID 26316549, compound

Product 1

HCID 69101849HCID 69101849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a round bottom flask was added triazole 24 (43.8 mg, 0.20 mmol, 1.0 eq.), DMF (2.0 mL), HOBt (29.7 mg, 0.22 mmol, 1.1 eq.), EDCI (42.0 mg, 0.22 mmol, 1.1 eq.), and triethylamine (0.076 mL, 0.60 mmol, 3.0 eq.). The reaction was stirred at RT for 30 min before adding 5-amino-2-chloro-benzotrifluoride (78.0 mg, 0.40 mmol, 2.0 eq.) and stirring overnight at RT. The reaction was quenched with water, extracted with EtOAc 3×, washed with 10% LiCl to remove DMF, dried with Na2SO4, and then concentrated via rotary evaporation. Trituration with ether gave triazole 25 in only 80% purity. Further purification by prep HPLC then gave pure triazole 25 as a white solid (21 mg, 23% yield). LC/MSD (BP Series 1100 MSD) MS (ES+) m/z 397.0 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.56 (br. s, 1H), 9.17 (s, 2H), 8.25 (d, 1H), 7.95 (dd, 1H), 7.69 (d, 1H), 7.49 (t, 1H), 7.43 (m, 1H), 7.33 (dd, 1H), 7.10 (dd, 1H), 4.84 (s, 2H) ppm.

Workup

  1. stirringstirring overnight at RT
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc 3×
  4. washwashed with 10% LiCl
  5. customto remove DMF
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated via rotary evaporation

Sources & evidence

ORD record
ord-12a6e6c9237042fa83d232c631b592c6
Source dataset
uspto-grants-2013_01
Patent number
US08362017B2

Reaction notes

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