Triethylamine → 5-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide

HRID 408856

反応式

HRID 408856 の反応式
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[F:11].[C:12]([NH:16][C:17]([C:19]1[O:20][C:21]([CH2:24][N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:22][CH:23]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>ClCCl>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:28]2[CH2:29][CH2:30][N:25]([CH2:24][C:21]3[O:20][C:19]([C:17]([NH:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])=[CH:23][CH:22]=3)[CH2:26][CH2:27]2)=[O:8])=[CH:4][C:3]=1[F:11]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 66661240N-tert-butyl-5-(piperazin-1-ylmethyl)furan-2-carboxamide

生成物 1

HCID 666615235-((4-(4-Amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylfuran-2-carboxamide収率 40.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 4-amino-3-fluorobenzoic acid (0.883 g, 5.69 mmol), N-tert-butyl-5-(piperazin-1-ylmethyl)furan-2-carboxamide (1.51 g, 5.69 mmol) and triethyl-amine (0.576 g, 5.69 mmol, 0.791 mL) in dichloromethane was added 1-propanephosphonic acid cyclic anhydride (3.62 g, 5.69 mmol, 3.39 mL, 50% solution in ethyl acetate). The reaction was stirred for 2 hours then concentrated under reduced pressure. The residue was taken up in ethyl acetate, washed with sodium bicarbonate, water and brine. The organic phase was concentrated under reduced pressure to give the title compound (0.93 g). MS (ESI) m/z 403.6 [M+H]+

後処理

  1. concentrationthen concentrated under reduced pressure
  2. washwashed with sodium bicarbonate, water and brine
  3. concentrationThe organic phase was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-9cc62522761947f9889e7d087f48d5f3
出典データセット
uspto-grants-2014_06
特許番号
US08759352B2

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