4-Piperidinamine → N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-5-((4-aminopiperidin-1-yl)methyl)pyrrolo[1,2-f][1,2,4]triazin-4-amine

HRID 1829917ノート

反応式

HRID 1829917 の反応式
C1(S([CH2:9][C:10]2[CH:11]=[CH:12][N:13]3[C:18]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)=[C:22]([Cl:35])[CH:21]=2)=[N:16][CH:15]=[N:14]3)=O)C=CC=CC=1.[NH2:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>C(Cl)Cl>[NH2:36][CH:37]1[CH2:42][CH2:41][N:40]([CH2:9][C:10]2[CH:11]=[CH:12][N:13]3[C:18]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=4)=[C:22]([Cl:35])[CH:21]=2)=[N:16][CH:15]=[N:14]3)[CH2:39][CH2:38]1

参加物

4

反応物 2

HCID 4243614-PiperidinamineHCID 22055282(5-Benzenesulfinylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-[3-chloro-4-(3-fluoro-benzyloxy)-phenyl]-amine

生成物 1

HCID 11698674N-(4-(3-fluorobenzyloxy)-3-chlorophenyl)-5-((4-aminopiperidin-1-yl)methyl)pyrrolo[1,2-f][1,2,4]triazin-4-amine収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
135 °C

実験手順

A mixture of the sulfoxide 7B (100 mg, 0.20 mmol) and 4-aminopiperidine (0.6 gm, 6 mmol) was heated in a sealed tube at 135° C. for 4 hr. The reaction mixture was taken up in DCM, washed with water, and dried (Na2SO4). Removal of the solvent followed by radial chromatography (2 mm silica gel plate eluted with DCM containing 5% MeOH) afforded 7C (40 mg, 42%) as a foam. Analytical HPLC retention time=1.35 min. (YMC Xterra S7 C18, 3.0×50 mm column, 10–90% aqueous methanol over 2 minutes containing 0.1% TFA, 5 mL/min, monitoring at 220 nm) and a LC/MS M++1=481.

後処理

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customRemoval of the solvent
  4. washfollowed by radial chromatography (2 mm silica gel plate eluted with DCM containing 5% MeOH)

出典と根拠

ORDレコード
ord-f59592f7d0414f7d9f06ffdffb18f64e
出典データセット
uspto-grants-2006_06
特許番号
US07064203B2

反応ノート

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