Formaldehyde → 2-[5-difluoromethoxy-1-(1-methyl-piperidin-4-yl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

HRID 246304노트

반응식

HRID 246304 반응식
Cl.[C:2]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH:28]([F:30])[F:29])[CH:25]=4)[N:20]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)[N:19]=3)[N:16]=2)[N:11]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:10]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[CH2:45](N(CC)CC)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:2]([NH:6][C:7]([C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH:28]([F:29])[F:30])[CH:25]=4)[N:20]([CH:31]4[CH2:32][CH2:33][N:34]([CH3:45])[CH2:35][CH2:36]4)[N:19]=3)[N:16]=2)[N:11]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:10]=1)=[O:8])([CH3:5])([CH3:4])[CH3:3]

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 712798372-(5-difluoromethoxy-1-piperidin-4-yl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide hydrochloride

생성물 1

HCID 712801622-[5-difluoromethoxy-1-(1-methyl-piperidin-4-yl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

In a round-bottomed flask, 2-(5-difluoromethoxy-1-piperidin-4-yl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide hydrochloride (91 mg, 0.14 mmol) was suspended in 1,2-dichloroethane (1.5 ml) and triethylamine (0.03 ml, 0.22 mmol) was added. The mixture was stirred room temperature for 10 min then formaldehyde (37% aqueous solution, 13 μl, 0.175 mmol) and sodium triacetoxyborohydride (119 mg, 0.56 mmol) were added. The yellow suspension was stirred at room temperature for 1.5 h then quenched with saturated aqueous NaHCO3 and extracted with dichloromethane (3×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated to afford 2-[5-difluoromethoxy-1-(1-methyl-piperidin-4-yl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a yellow foam which was used without further purification.

후처리

  1. stirringThe yellow suspension was stirred at room temperature for 1.5 h
  2. customthen quenched with saturated aqueous NaHCO3
  3. extractionextracted with dichloromethane (3×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8c2163271ec548519c640d25344ae30f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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