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Trifluoroacetic acid → (R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

HRID 2275046
ノート
印刷プレビュー

反応式

HRID 2275046 の反応式
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1
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 2

HCID 6422Trifluoroacetic acidHCID 118178622(R)-tert-Butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate

生成物 1

HCID 73052939(R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

To a solution of (R)-tert-butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate (1.5587 g, 2.79 mmol) in DCM (10 ml) was added TFA (5 mL, 65.3 mmol) dropwise. The reaction mixture was stirred for 30 minutes and then concentrated under vacuum to afford an oil. The oil was dissolved in methanol and loaded onto a 70 g SCX cartridge. The column was washed with MeOH (2CV) and the product collected as the free base with 2M ammonia in methanol (3CV). The product was concentrated in vacuo yield a crude product. This was purified by high pH MDAP (Method E). Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a white solid, 1.127 g.

後処理

  1. concentrationconcentrated under vacuum
  2. customto afford an oil
  3. washThe column was washed with MeOH (2CV)
  4. customthe product collected as the free base with 2M ammonia in methanol (3CV)
  5. concentrationThe product was concentrated in vacuo
  6. customyield a crude product
  7. customThis was purified by high pH MDAP (Method E)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-37ec4487544742439e83139f93573e9a
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09127003B2

反応ノート

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