Hydrochloric Acid → N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride

HRID 246716ノート

反応式

HRID 246716 の反応式
[Si]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([CH3:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)=[O:15])([CH3:12])[CH3:11])(C(C)(C)C)(C)C.[ClH:62]>O1CCOCC1>[ClH:62].[OH:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N:21][C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([CH3:34])=[CH:31][CH:32]=4)[N:27]([CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)[N:26]=3)=[CH:23][N:24]=[C:19]2[NH:18][CH:17]=1)=[O:15])([CH3:12])[CH3:11]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 71280346N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

生成物 1

HCID 71280460N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride収率 64%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (167 mg, 0.2 mmol) in dioxane (20 mL) was bubbled HCl gas until saturation and then stirred at room temperature for 16 hours. Reaction mixture was concentrated and the residue was triturated with methanol (1 mL) then decanted and dried to afford N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (76 mg, 64%) as a white solid. LCMS: (M+H)+=478; 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 8.29 (s, 1H), 7.56 (s, 1H), 7.22 (d, 1H, J=8.1 Hz), 5.00-4.96 (m, 2H), 4.08-3.85 (m, 12H), 2.59 (s, 3H), 1.56 (s, 6H).

後処理

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customthe residue was triturated with methanol (1 mL)
  4. customthen decanted
  5. customdried

出典と根拠

ORDレコード
ord-d50f42095ab54f63a01d3197cf50b0d5
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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