1-Hydroxybenzotriazole → HCID 69200824, compound

HRID 2114145Notes

Reaction equation

HRID 2114145 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH:18]3[CH2:20][CH2:19]3)=[O:15])=[CH:10][CH:9]=2)[CH:7]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[N:34]=[C:33]([C:35](O)=[O:36])[CH:32]=[N:31][CH:30]=2)=[CH:25][CH:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.C(OCC)(=O)C>[CH:18]1([CH2:17][NH:16][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]3[C:5]([CH3:21])=[CH:4][CH:3]=[C:2]([NH:1][C:35]([C:33]4[CH:32]=[N:31][CH:30]=[C:29]([C:26]5[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=5)[N:34]=4)=[O:36])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113004885'-amino-N-(cyclopropylmethyl)-2'-methyl-1,1'-biphenyl-4-carboxamideHCID 692039636-(4-Fluorophenyl)-2-pyrazinecarboxylic acid

Product 1

HCID 69200824HCID 69200824, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl4-carboxamide (75 mg, 0.27 mmol), 6-(4fluorophenyl)pyrazine-2-carboxylic acid (58.4 mg, 0.27 mmol), HATU (101.5 mg, 0.27 mmol), HOBT (36 mg, 0.27 mmol) and DIPEA (140 μl, 0.80 mmol) in DMF (3 ml) were stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (150 ml), washed with hydrochloric acid (0.5M, 2×20ml), aqueous sodium hydrogen carbonate (20 ml) and dried (magnesium sulphate). Evaporation of the solvents under vacuum gave N-(4′-{[(cyclopropylmethyl)amino]carbonyl}-6-methyl-1,1′-biphenyl-3-yl)-6-(4-fluorophenyl)pyrazine-2-carboxamide (117 mg, 91%). NMR; δH [2H6]—DMSO 10:64,(1H, s), 9.52,(1H, s), 9.20,(1H, s), 8.63,(1H, t), 8.54,(2H, m), 7.95,(2H, d), 7.88,(1H, dd), 7.78,(1H, d), 7.48,(2H, d), 7.42,(2H, t), 7.35,(1H, d), 3.17,(2H, t), 2.23,(3H, s), 1.05,(1H, m), 0.24,(2H, m). LCMS: retention time 3.65 min, MH+481.

Workup

  1. washwashed with hydrochloric acid (0.5M, 2×20ml), aqueous sodium hydrogen carbonate (20 ml)
  2. dry with materialdried (magnesium sulphate)
  3. customEvaporation of the solvents under vacuum

Sources & evidence

ORD record
ord-20df778a3d514a86bb3c683e41ab07ba
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

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