Formaldehyde → 5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246511ノート

反応式

HRID 246511 の反応式
C([NH:5][C:6]([C:8]1[C:16]2[C:11](=[N:12][CH:13]=[C:14](C3C4C(=CC=C(OC(F)F)C=4)N(CC4OCCNC4)N=3)[N:15]=2)[N:10]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:9]=1)=[O:7])(C)(C)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:42][Si:41]([CH3:44])([CH3:43])[CH2:40][CH2:39][O:38][CH2:37][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][N:15]=[C:16]2[C:8]([C:6]([NH2:5])=[O:7])=[CH:9]1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 71279850N-tert-butyl-2-(5-(difluoromethoxy)-1-(morpholin-2-ylmethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

生成物 1

HCID 866779835-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide収率 135.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a stirred solution of N-tert-butyl-2-(5-(difluoromethoxy)-1-(morpholin-2-ylmethyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (100 mg, 159 μmol) in methanol (4 mL), cooled to 0° C. with ice bath, was added aqueous formaldehyde (1 mL, 13.4 mmol), followed by the addition of sodium triacetoxyborohydride (75.7 mg, 357 μmol). The reaction mixture was stirred at room temperature for 15 h then concentrated in vacuo. Purification by chromatography (silica, 4 g Analogix column, 0-10% methanol containing 10% ammonium hydroxide in dichloromethane) gave N-tert-butyl-2-(5-(difluoromethoxy)-1-(4-methylmorpholin-2-yl)methyl)-1H-indazol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (63 mg, 62%). MS (M+H)+=644.

後処理

  1. concentrationthen concentrated in vacuo
  2. customPurification by chromatography (silica, 4 g Analogix column, 0-10% methanol containing 10% ammonium hydroxide in dichloromethane)

出典と根拠

ORDレコード
ord-95249ac262494d1782262f191e4d5874
出典データセット
uspto-grants-2014_02
特許番号
US08658646B2

反応ノート

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