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

HRID 526309

반응식

HRID 526309 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-289c97a6f52141fc912f358ed0430c84
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345905B2

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