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Formaldehyde → N-(3-(5-fluoro-1-methylindolin-6-yl)-1-(1-methylazetidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

HRID 331066
ノート
印刷プレビュー

反応式

HRID 331066 の反応式
[NH:1]1[CH2:4][CH:3]([N:5]2[C:9]3=[N:10][CH:11]=[CH:12][C:13]([NH:14][S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:17])=[O:16])=[C:8]3[C:7]([C:24]3[CH:32]=[C:31]4[C:27]([CH2:28][CH2:29][N:30]4[CH3:33])=[CH:26][C:25]=3[F:34])=[CH:6]2)[CH2:2]1.C=O.[C:37]([BH3-])#N.[Na+]>C(Cl)Cl>[F:34][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][C:24]=1[C:7]1[C:8]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[NH:14][S:15]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)(=[O:17])=[O:16])[N:5]([CH:3]3[CH2:2][N:1]([CH3:37])[CH2:4]3)[CH:6]=1)[N:30]([CH3:33])[CH2:29][CH2:28]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 71090140N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

生成物 1

HCID 71090287N-(3-(5-fluoro-1-methylindolin-6-yl)-1-(1-methylazetidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of N-(1-(azetidin-3-yl)-3-(5-fluoro-1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)benzenesulfonamide D34 (394 mg, 0.825 mmol) in DCM (5 mL) was added formaldehyde (0.307 mL, 4.13 mmol) and sodium cyanoborohydride (104 mg, 1.650 mmol). The final mixture was stirred at RT for 1 h. The mixture was passed through a SCX cartridge eluting with MeOH and followed by 2M ammonia in MeOH. The desired fractions were concentrated and further purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-10%) to give the title compound (153 mg). LCMS (A): m/z (M+H)+ 492, C26H26FN5O2S requires 491 (acidic).

後処理

  1. washeluting with MeOH
  2. concentrationThe desired fractions were concentrated
  3. customfurther purified on normal phase silica eluting with 2M ammonia in MeOH and DCM (0-10%)

出典と根拠

ORDレコード
ord-a3c8330bc6464f6aafe443a0e8ee780f
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877742B2

反応ノート

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