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Sodium borohydride → 5-[3-chloro-2-cyano-5-(1-hydroxyethyl)-6-methoxyphenyl]N,N-dimethylpyridine-2-carboxamide

HRID 1499897
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HRID 1499897 반응식
[BH4-].[Na+].[C:3]([C:6]1[C:7]([O:26][CH3:27])=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[N:19][CH:20]=2)[C:9]([C:13]#[N:14])=[C:10]([Cl:12])[CH:11]=1)(=[O:5])[CH3:4]>CO>[Cl:12][C:10]1[C:9]([C:13]#[N:14])=[C:8]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([N:23]([CH3:25])[CH3:24])=[O:22])=[N:19][CH:20]=2)[C:7]([O:26][CH3:27])=[C:6]([CH:3]([OH:5])[CH3:4])[CH:11]=1
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4

반응물 2

HCID 4311764Sodium borohydrideHCID 866778195-(3-acetyl-5-chloro-6-cyano-2-methoxyphenyl)-N,N-dimethylpyridine-2-carboxamide

생성물 1

HCID 866778205-[3-chloro-2-cyano-5-(1-hydroxyethyl)-6-methoxyphenyl]N,N-dimethylpyridine-2-carboxamide수율 100%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

Sodium tetrahydroborate (320 mg, 8.4 mmol) was added to a mixture of 5-(3-acetyl-5-chloro-6-cyano-2-methoxyphenyl)-N,N-dimethylpyridine-2-carboxamide (2 g, 6 mmol) in methanol (100 mL) cooled at 0° C. The reaction was stirred at 0° C. for 1 h, quenched with water and partitioned between water and EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered and concentrated to give crude 5-[3-chloro-2-cyano-5-(1-hydroxyethyl)-6-methoxyphenyl]-N,N-dimethylpyridine-2-carboxamide as clear oil (2.0 g, 100%). LCMS calculated for C18H19ClN3O3 (M+H)+: m/z=360.1; found: 360.1.

후처리

  1. customquenched with water
  2. custompartitioned between water and EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-62271038140b4ea7aa3b3146658b14c6
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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