Sodium Carbonate → HCID 178505812、化合物

HRID 45895

反応式

HRID 45895 の反応式
C([N:8](CC1C=CC=CC=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:27])C1C=CC=CC=1.[F:35][C:36]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:37]=1[CH:38]=O.C([BH3-])#N.[Na+].C([O-])([O-])=O.[Na+].[Na+]>CO.C(O)(=O)C.O>[F:35][C:36]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][C:37]=1[CH2:38][NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:27]

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 1376632,5-DifluorobenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178505869HCID 178505869、化合物

生成物 1

HCID 178505812HCID 178505812、化合物収率 85%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

Dibenzyl-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine (prepared as described in Example 22) (150 mg, 0.551 mmol) was dissolved in a 1:1:1 mixture of methanol, acetic acid and water (18 mL). Freshly distilled 2,5-difluorobenzaldehyde (0.180 mL, 1.653 mmol, 3 eq) was then added, followed by sodiumcyanoborohydride (2.424 mmol, 4.4 eq) and the mixture was stirred at room temperature for 5 hours. It was then poured into water, basified to pH 10 by addition of a saturated aqueous solution of Na2CO3 and extracted with ethyl acetate (3×30 mL). The combine dorganic layers were washed with brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by flash chromatography on silica gel (DCM/MeOH 96:4) to give 124 mg (85%) of (2,5-difluoro-benzyl)-[2,4-difluoro-3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-phenyl]-amine a white solid.

後処理

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe combine dorganic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude product was purified by flash chromatography on silica gel (DCM/MeOH 96:4)

出典と根拠

ORDレコード
ord-9749bc73eb07490ca8a3512677aea7ec
出典データセット
uspto-grants-2013_09
特許番号
US08541575B2

関連ノート

読み込み中…