Diethyl Ether → Zeneca ZM 224832

HRID 1111328노트

반응식

HRID 1111328 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 195507Zeneca ZM 224832수율 77%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e2df3113f06e40f8943cad1f83c218d0
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980352

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