Triethylamine → HCID 10005193, compound

HRID 1975419Notes

Reaction equation

HRID 1975419 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[CH:8]=[C:7]2[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[O:25][CH3:26])([OH:3])=O.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.Cl.[F:47][C:48]([F:55])([F:54])[CH2:49][CH:50]([CH3:53])[CH2:51][NH2:52]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[CH2:14][C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([C:1](=[O:3])[NH:52][CH2:51][CH:50]([CH3:53])[CH2:49][C:48]([F:55])([F:54])[F:47])[CH:5]=2)[N:9]([CH3:13])[CH:8]=1)[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9998178Methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoateHCID 21841122136564-89-1

Product 1

HCID 10005193HCID 10005193, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of methyl 4-(5-carboxy-1-methylindol-3-ylmethyl)-3-methoxybenzoate (2.0 g), 4-dimethylaminopyridine (0.71 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.3 g), triethylamine (1.0 mL) and 4,4,4-trifluoro-2-methylbutylamine hydrochloride (1.2 g) in methylene chloride (28 mL) was stirred under a nitrogen atmosphere for 18 hours. The mixture was diluted with methylene chloride, washed (10% (w/v) hydrochloric acid, water and brine), dried (MgSO4), and evaporated. The resulting ivory foam was purified by flash chromatography, eluting with 1:1 ethyl acetate:hexane to afford methyl 3-methoxy-4-[1-methyl-5-(2-methyl-4,4,4-trifluorobutylcarbamoyl)indol-3-ylmethyl]benzoate as a white powder (2.2g, 82%); mp 168°-170° C.; partial NMR (300 MHz, CDCl3): 1.12 (d, 3H, CHCH3), 2.00 (m, 1H), 2.22 (m, 2H), 3.34-3.52 (m, 2H, NCH2), 3.75 (s, 3H, NCH3), 3.90 (s, 3H, CO2CH3), 3.93 (s, 3H, OCH3), 4.13 (s, 2H, CH2), 6.21 (t, 1H, NH), 6.82 (s, 1H, indole-H(2)), 8.02 (s, 1H, indole-H(4)).

Workup

  1. washwashed (10% (w/v) hydrochloric acid, water and brine)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe resulting ivory foam was purified by flash chromatography
  5. washeluting with 1:1 ethyl acetate

Sources & evidence

ORD record
ord-f5f16885d2e74954bdeaf37a19e1b78c
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

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