Tert-Butylamine → HCID 70983812, compound

HRID 338884Notes

Reaction equation

HRID 338884 reaction equation
[CH:1]1([C:4]2[C:5]([C:15]([OH:17])=O)=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[C:11]([CH3:14])[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.[CH3:18][C:19]([NH2:22])([CH3:21])[CH3:20].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[C:19]([NH:22][C:15]([C:5]1[C:4]([CH:1]2[CH2:2][CH2:3]2)=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([CH3:14])=[N:12]2)=[CH:7][CH:6]=1)=[O:17])([CH3:21])([CH3:20])[CH3:18]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70983733HCID 70983733, compound

Product 1

HCID 70983812HCID 70983812, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-cyclopropyl-2-methylquinoline-7-carboxylic acid (0.050 g, 0.220 mmol) and 2-methylpropan-2-amine (0.116 mL, 1.10 mmol) in DMF (1 mL) was added HATU (0.125 g, 0.33 mmol) at ambient temperature and the reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was purified directly by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 25M column, 0-90% CH3CN/water gradient; 25 column volumes) to give N-tert-butyl-8-cyclopropyl-2-methylquinoline-7-carboxamide (0.033 g, 53.1%) as a solid.

Workup

  1. customThe reaction mixture was purified directly by C-18 reverse phase flash chromatography (Biotage SP4 unit

Sources & evidence

ORD record
ord-fc6c1753c1ea450ebe847cb2124b2ae9
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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