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Hydrochloric Acid → N-(4,4-dimethylcyclohexyl)-4,6-difluoro-1H-indole-2-carboxamide

HRID 62660
ノート
印刷プレビュー

反応式

HRID 62660 の反応式
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=O)[NH:6]2.[CH3:15][C:16]1([CH3:23])[CH2:21][CH2:20][CH:19]([NH2:22])[CH2:18][CH2:17]1.Cl.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:15][C:16]1([CH3:23])[CH2:21][CH2:20][CH:19]([NH:22][C:12]([C:5]2[NH:6][C:7]3[C:3]([CH:4]=2)=[C:2]([F:1])[CH:10]=[C:9]([F:11])[CH:8]=3)=[O:14])[CH2:18][CH2:17]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 4210544,4-Dimethylcyclohexan-1-amineHCID 34514414,6-difluoro-1H-indole-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 72711190
N-(4,4-dimethylcyclohexyl)-4,6-difluoro-1H-indole-2-carboxamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4,6-difluoro-1H-indole-2-carboxylic acid (5 g, 25.36 mmol×4 batches) and 4,4-dimethylcyclohexylamine.HCl (I-6b: 4.6 g, 28.10 mmol, for each batch) in dry DMF (75 mL) was cooled to 0° C. and HATU (11.62 g, 30.57 mmol, for each batch) was added followed by DIPEA (22 mL, 127.9 mmol, for each batch) drop-wise and the mixture was stirred under inert atmosphere at room temperature for 17h. Ice-cold water (50 mL) was added to the reaction mixture with vigorous stirring. The precipitated solid was collected by filtration and dried thoroughly. The crude compound obtained from combining all the batches was purified by column chromatography over silica gel (100-200 mesh) using a solvent gradient of 30%-40% ethyl acetate in hexanes as eluent to afford 23 g of off-white solid. It was triturated with ether/hexanes (3:7) in five cycles to afford 20.6 g (66.2%) of 4,6-difluoro-N-(4,4-dimethylcyclohexyl)-1H-indole-2-carboxamide (2A) as an white solid.

後処理

  1. filtrationThe precipitated solid was collected by filtration
  2. customdried thoroughly
  3. customThe crude compound obtained
  4. customwas purified by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-abc1b8fcc0b841ddae7184ed5c8b7e43
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447039B2

反応ノート

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