Triethylamine → HCID 178426492, compound

HRID 707316Notes

Reaction equation

HRID 707316 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C@H:11]2[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13][CH2:12]2)=[N:8][CH:9]=1.[Cl:18][C:19]1[C:20]([C:25]([CH3:30])([CH3:29])[C:26](O)=[O:27])=[N:21][CH:22]=[CH:23][N:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[Cl:18][C:19]1[C:20]([C:25]([CH3:30])([CH3:29])[C:26]([NH:17][C@H:14]2[CH2:15][CH2:16][C@H:11]([NH:10][C:7]3[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][N:8]=3)[CH2:12][CH2:13]2)=[O:27])=[N:21][CH:22]=[CH:23][N:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acid2×HCID 178426489HCID 178426489, compound2×

Product 1

HCID 178426492HCID 178426492, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask was added trans-N1-(5-methylpyridin-2-yl)cyclohexane-1,4-diamine dihydrochloride (intermediate 31, 0.2108 g, 0.758 mmol), 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (intermediate 29, 0.182 g, 0.909 mmol), HATU (0.375 g, 0.985 mmol), and triethylamine (0.422 ml, 3.03 mmol) in dichloromethane (1.515 ml) to stir at room temperature. After 4 hours the solvent was evaporated off. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (25 g), eluting with a gradient of 0% to 5% methanol in dichloromethane, to provide 2-(3-chloropyrazin-2-yl)-2-methyl-N-(trans-4-((5-methylpyridin-2-yl)amino)cyclohexyl)propanamide (0.2148 g, 0.554 mmol, 73.1% yield).

Workup

  1. customAfter 4 hours the solvent was evaporated off
  2. customchromatographed through a Biotage SNAP HP-silica gel column (25 g)
  3. washeluting with a gradient of 0% to 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-45c6e23baea14998b54b1d578cd024c5
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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