Sodium Bicarbonate → 2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-hydroxymethyl-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17463

反応式

HRID 17463 の反応式
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:24]#[N:25])[C:10]([CH3:23])=[C:11]([CH:21]=[O:22])[C:12]=3[N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)[N:8]=2)[CH2:3][CH2:2]1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>CO.ClCCl>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:24]#[N:25])[C:10]([CH3:23])=[C:11]([CH2:21][OH:22])[C:12]=3[N:13]3[CH2:17][CH2:16][C@H:15]([N:18]([CH3:20])[CH3:19])[CH2:14]3)[N:8]=2)[CH2:2][CH2:3]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride2 回HCID 866308522-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile

生成物 1

HCID 685869932-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-hydroxymethyl-5-methyl-1,3-benzoxazole-4-carbonitrile収率 76.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

2-Cyclopropyl-7-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile (free form of #88) (120 mg, 0.35 mmol) was dissolved in methanol (2.4 ml) and dichloromethane (0.8 ml), then at 0° C., sodium borohydride (18 mg, 0.43 mmol) was added, followed by stirring at the same temperature for 1 hour. Next, at the same temperature, sodium borohydride (9 mg, 0.22 mmol) was further added, followed by stirring at the same temperature for 1 hour. An aqueous saturated sodium hydrogencarbonate solution was added, followed by farmer stirring for 5 minutes. The solution was extracted three times with chloroform. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1) to obtain the entitled compound (91 mg) as a roughly-purified product. This was washed with isopropyl ether to obtain the entitled compound (85 mg, 70%) as a white solid.

後処理

  1. stirringby stirring at the same temperature for 1 hour
  2. stirringstirring for 5 minutes
  3. extractionThe solution was extracted three times with chloroform
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe insoluble matter was separated by filtration
  7. customthe solvent was evaporated away
  8. customthe resulting residue was purified by preparative TLC (eluent, chloroform:methanol=9:1)

出典と根拠

ORDレコード
ord-f3a71063c91b448495867d1cb6763889
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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