1-Hydroxybenzotriazole → HCID 69202455, compound

HRID 2114146Notes

Reaction equation

HRID 2114146 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.[N:22]1([C:28]2[N:33]=[C:32]([C:34](O)=[O:35])[CH:31]=[N:30][CH:29]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]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:34]([C:32]4[CH:31]=[N:30][CH:29]=[C:28]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)[N:33]=4)=[O:35])[CH:7]=3)=[CH:9][CH:10]=2)=[O:15])[CH2:20][CH2:19]1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27625626-morpholin-4-ylpyrazine-2-carboxylic AcidHCID 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-carboxamide

Product 1

HCID 69202455HCID 69202455, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5′-Amino-N-(cyclopropylmethyl)-2′-methyl-1,1′-biphenyl-4carboxamide (75 mg, 0.27 mmol), 6-morpholin-4-ylpyrazine-2-carboxylic acid (55.9 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, 2×20 ml), 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-morpholin-4-ylpyrazine-2-carboxamide (118 mg, 94%). NMR; δH [2H6]—DMSO 10.17,(1H, s), 8.62,(1H, t), 8.54,(1H, s), 8.47,(1H, s), 7.93,(2H, d), 7.80,(1H, dd), 7.70,(1H, d), 7.45,(2H, d), 7.31,(1H, d), 3.73,(8H, m), 3.16,(2H, t), 2.21,(3H, s), 1.04,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS: retention time 3.20 min, MH+472.

Workup

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

Sources & evidence

ORD record
ord-d8e35d8d34a8444ea12b5ec8a02aa6eb
Source dataset
uspto-grants-2008_10
Patent number
US07432289B2

Reaction notes

Loading…