1H-Indole-2-carboxylic acid, 1-methyl- → HCID 86583991, compound

HRID 634912Notes

Reaction equation

HRID 634912 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([OH:13])=O.N[C@H](C([C@H:19]([CH:33]=[O:34])[CH:20](N)[C:21](=[N:27][NH:28][C:29]([NH2:31])=[O:30])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O)C.[OH2:35].O[N:37]1[C:41]2C=CC=[CH:45][C:40]=2[N:39]=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.C(OCC)(=O)C.CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[C:11]([NH:39][C@H:40]([C:41]([NH:37][C@H:19]([CH:33]=[O:34])[CH2:20][C:21](=[N:27][NH:28][C:29]([NH2:31])=[O:30])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:35])[CH3:45])=[O:13]

Participants

8

Reactant 4

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86583992HCID 86583992, compound

Product 1

HCID 86583991HCID 86583991, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Methylindole-2-carboxylic acid (107 mg, 0.6 mmol) and (3S)-3-(alaninyl)-amino-4-oxobutanoic acid, t-butyl ester semicarbazone (188 mg, 96%, 0.6 mmol) were dissolved in DMF (2 mL) then both 1-hydroxybenzotriazole-hydrate (96 mg, 0.63 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDAC) (161 mg, 0.84 mmol) was added to the resultant mixture under a nitrogen atmosphere at 0° C. Stirring was continued for 1 hour at 0° C. and an additional 20 hours at room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated to give a yellow solid. Trituration of the solid with ether afforded the title product as a slightly yellow powder (213 mg, 77%). TLC methanol/methylene chloride: 1/9, silica gel):Rf=0.47; 1H-NMR (CDCl3+CD3OD): δ 7.96 (d, J=8.0, 1H). 7.57-7.67 (m, 2H), 7.31-7.42 (m, 2H), 7.13-7.19 (m, 2H), 7.06 (s, 1H), 4.91 (m, 1H), 4.65 (q, J=7.1, 1H), 4.01 (s, 3H), 2.59-2.78 (m, J=5.6, 15.7, 2H), 1.49 (d, J=7.1, 3H), 1.39 (s, 9H).

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customto give a yellow solid

Sources & evidence

ORD record
ord-745f2dca7b824ec7b723fe42423d34c4
Source dataset
uspto-grants-2001_02
Patent number
US06184244B2

Reaction notes

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