Tert-Butylamine → HCID 70654277, compound

HRID 1405310Notes

Reaction equation

HRID 1405310 reaction equation
[C@H:1]([N:5]([CH3:26])[C:6]1[C:7]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[N:8][C:9]2[C:14]([N:15]=1)=[CH:13][C:12]([C:16](O)=[O:17])=[CH:11][CH:10]=2)([CH2:3][CH3:4])[CH3:2].C(N(CC)CC)C.[CH3:34][C:35]([NH2:38])([CH3:37])[CH3:36].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[C:35]([NH:38][C:16]([C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:6]([N:5]([C@@H:1]([CH2:3][CH3:4])[CH3:2])[CH3:26])=[N:15]2)=[O:17])([CH3:37])([CH3:36])[CH3:34]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 70654327HCID 70654327, compound

Product 1

HCID 70654277HCID 70654277, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-(sec-butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxylic acid (500 mg, 1.42 mmol) in dichloromethane (30 mL) was added triethylamine (348 mg, 3.44 mmol), 2-methylpropan-2-amine (197 mg, 2.7 mmol), and T3P (12 mL), and the reaction mixture was stirred overnight at room temperature. The resulting solution was diluted with water (150 mL) and extracted with dichloromethane (4×50 mL), the organic layers combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to afford (R)—N-tert-butyl-3-(sec-butyl(methyl)amino)-2-(4-fluorophenyl)quinoxaline-6-carboxamide as a yellow solid (750 mg, crude).

Workup

  1. extractionextracted with dichloromethane (4×50 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-301a384ceadf4abf8ced94a7367fb1de
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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