Tert-Butylamine → N-tert-butyl-2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide

HRID 1405313Notes

Reaction equation

HRID 1405313 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18][C:17]4[C:12](=[CH:13][CH:14]=[C:15]([C:25](O)=[O:26])[CH:16]=4)[N:11]=3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.C(N(CC)CC)C.[CH3:35][C:36]([NH2:39])([CH3:38])[CH3:37].C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl.O>[C:36]([NH:39][C:25]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:6]1[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[CH:3]3)[C:19]([N:20]([CH3:24])[CH:21]([CH3:23])[CH3:22])=[N:18]2)=[O:26])([CH3:38])([CH3:37])[CH3:35]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 509916592-(1H-indazol-5-yl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylic acid

Product 1

HCID 70654225N-tert-butyl-2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylic acid (200 mg, 0.55 mmol) in dichloromethane (30 ml) was added triethylamine (210 mg, 2.08 mmol), 2-methylpropan-2-amine (121 mg, 1.65 mmol), and T3P (396 mg, 1.25 mmol), and the resulting mixture was stirred for 1 h at room temperature. The solution was diluted with water (150 ml), extracted with dichloromethane (3×50 ml), dried over anhydrous magnesium, and concentrated in vacuo to get N-tert-butyl-2-(1H-indazol-5-yl)-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxamide as a yellow solid (311 mg, crude).

Workup

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

Sources & evidence

ORD record
ord-f55e8946de4440fa9cd57b867f101943
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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