Acetic Acid → HCID 89442445、化合物

HRID 632723ノート

反応式

HRID 632723 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH2:20])=[N:10][CH:11]=[N:12][C:13]=2[N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:29]([Cl:30])=[CH:28][C:25]([CH:26]=O)=[C:24]([OH:31])[CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[NH2:20][C:9]1[N:10]=[CH:11][N:12]=[C:13]([N:14]2[CH2:19][CH2:18][N:17]([CH2:26][C:25]3[CH:28]=[C:29]([Cl:30])[C:22]([Cl:21])=[CH:23][C:24]=3[OH:31])[CH2:16][CH2:15]2)[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5283894,5-Dichloro-2-hydroxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 89442443HCID 89442443、化合物

生成物 1

HCID 89442445HCID 89442445、化合物収率 80.7%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

A reaction mixture of 5-(4-fluoro-phenyl)-6-piperazin-1-yl-pyrimidin-4-ylamine (400.0 mg; 1.46 mmol; 1.00 eq.), 4,5-dichloro-2-hydroxy-benzaldehyde (279.5 mg; 1.46 mmol; 1.00 eq.), Acetic acid (87.8 mg; 1.46 mmol; 1.00 eq.) and sodium triacetoxy borohydride (926.1 mg; 4.39 mmol; 3.00 eq.) in DCE (10 ml) was stirred overnight at RT. The reaction solution was diluted with DCM and washed with brine. The organic layer was dried and concentrated, which was added 10 ml of ether and stirred for 5 mins. The precipitate was filtered to afford the title as white off solid (528 mg, yield 80.5%). LC-MS: (M+1=448, obsd.=448/450).

後処理

  1. washwashed with brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. additionwhich was added 10 ml of ether
  5. stirringstirred for 5 mins
  6. filtrationThe precipitate was filtered

出典と根拠

ORDレコード
ord-a2798236ce7f480fbef594c7cd7ffd66
出典データセット
uspto-grants-2016_04
特許番号
US09321760B2

反応ノート

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