Methanamine, hydrochloride (1:1) → ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate

HRID 526309

反応式

HRID 526309 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:15][C:16]([OH:18])=O)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[CH3:19][N:20](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl-].C[NH3+].CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:19][NH:20][C:16](=[O:18])[CH2:15][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]=[C:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5]

参加物

7

反応物 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 183276071-(carboxy-methyl)-1H-indole-2-carboxylic ethyl ester

生成物 1

HCID 89601817ethyl 1-(2-(methylamino)-2-oxoethyl)-1H-indole-2-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-(2-(ethoxycarbonyl)-1H-indol-1-yl)acetic acid (3.78 g), HATU (6.98 g), methylammonium chloride, and Hunig's base (6.33 mL) in DMF (77 mL) was stirred at room temperature for 24 hr. The reaction was worked up by the addition of water and the aqueous phase was extracted with EtOAc (2×65 mL). The combined organic phase was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was purified by CombiFlash (0-100% EtOAc/hexane) to afford the title compound as a yellowish solid.

後処理

  1. extractionthe aqueous phase was extracted with EtOAc (2×65 mL)
  2. washThe combined organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by CombiFlash (0-100% EtOAc/hexane)

出典と根拠

ORDレコード
ord-289c97a6f52141fc912f358ed0430c84
出典データセット
uspto-grants-2016_05
特許番号
US09345905B2

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