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

HRID 526309

Reaction equation

HRID 526309 reaction equation
[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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-289c97a6f52141fc912f358ed0430c84
Source dataset
uspto-grants-2016_05
Patent number
US09345905B2

Linked notes

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