Diethyl Ether → Zeneca ZM 224832

HRID 1111328ノート

反応式

HRID 1111328 の反応式
[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH2:19])[CH3:16])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.[Br:20][C:21]1[C:22]([OH:34])=[C:23]([CH:32]=O)[C:24]2[CH2:25][CH2:26][C:27]([CH3:31])([CH3:30])[C:28]=2[CH:29]=1.[BH4-].[Na+].CCOCC>C(O)C.C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:10]([NH:12][CH2:13][CH2:14][N:15]([CH2:17][CH2:18][NH:19][CH2:32][C:23]2[C:22]([OH:34])=[C:21]([Br:20])[CH:29]=[C:28]3[C:24]=2[CH2:25][CH2:26][C:27]3([CH3:31])[CH3:30])[CH3:16])=[O:11])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 22152287HCID 22152287、化合物HCID 221522956-Bromo-1,1-dimethyl-5-hydroxyindan-4-carboxaldehyde

生成物 1

HCID 195507Zeneca ZM 224832収率 77%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 1.82 g (6.32 mmol) of 3,5-diamino-N-[2-[(2-aminoethyl)methylamino]ethyl]-6 -chloropyrazinecarboxamide (A) and 1.70 g (6.32 mmol) of 6-bromo-1,1-dimethyl-5-hydroxyindan-4-carboxaldehyde (B) in 70 ml of ethanol and 10 ml of methylene chloride was stirred at ambient temperature for 1 h. Sodium borohydride (0.29 g, 7.58 mmol) was added and the reaction mixture stirred for 15 min. The solution was evaporated and the residue was partitioned between water and methylene chloride The organic phase was dried and evaporated. The residue was chromatographed on silica gel (150 g) using 0.2:3:96.8 (v/v/v) ammonium hydroxide:methanol:methylene chloride as eluent. There was obtained 2.62 g (4.84 mmol, 77%) of the title compound after trituration with ether: mp 134°-136° C.

後処理

  1. stirringthe reaction mixture stirred for 15 min
  2. customThe solution was evaporated
  3. customthe residue was partitioned between water and methylene chloride The organic phase
  4. customwas dried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (150 g)

出典と根拠

ORDレコード
ord-e2df3113f06e40f8943cad1f83c218d0
出典データセット
uspto-grants-1990_12
特許番号
US04980352

反応ノート

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