Tert-Butylamine → (S)-N-tert-butyl-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxamide

HRID 1405307Notes

Reaction equation

HRID 1405307 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:22][CH2:21][CH2:20][C@@H:19]3[CH3:23])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:24](O)=[O:25])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH3:27][C:28]([NH2:31])([CH3:30])[CH3:29].C(N(CC)CC)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>ClCCl>[C:28]([NH:31][C:24]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:17]([N:18]1[CH2:22][CH2:21][CH2:20][C@@H:19]1[CH3:23])=[N:16]2)=[O:25])([CH3:30])([CH3:29])[CH3:27]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 50991311(S)-2-(4-Fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid

Product 1

HCID 70654210(S)-N-tert-butyl-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylic acid (200 mg, 0.57 mmol) in dichloromethane (30 mL) was added 2-methylpropan-2-amine (46 mg, 0.63 mmol), triethylamine (115 mg, 1.14 mmol) and T3P (217 mg, 0.68 mmol) dropwise with stifling. The resulting solution was stirred for 3 h at room temperature and then concentrated in vacuo to afford (S)—N-tert-butyl-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxamide as a yellow oil (160 mg, crude).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89b2f7bc7fcd49369e2e939f57fd2d4c
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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