Hydrochloric Acid → Methyl 4-[5-(2-cyclopentylacetamido)-1-methylindol-3-ylmethyl]-3-methoxybenzoate

HRID 1723223Notes

Reaction equation

HRID 1723223 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[C:5]2[CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[O:23][CH3:24].[CH:25]1([CH2:30][C:31](O)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26]1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.ClCCl>[CH:25]1([CH2:30][C:31]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH3:11])[CH:6]=[C:5]3[CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[O:23][CH3:24])=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 71606Cyclopentylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11209537Methyl 4-((5-amino-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoate

Product 1

HCID 14626822Methyl 4-[5-(2-cyclopentylacetamido)-1-methylindol-3-ylmethyl]-3-methoxybenzoateYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.57 g.), cyclopentylacetic acid (0.23 g.), 4-(dimethylamino)pyridine (0.22 g.), and 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride (0.343 g.), was dissolved in dichloromethane (25 ml.), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml.), the separated aqueous layer extracted with dichloromethane (3×25 ml.), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethyl acetate to give the title compound (0.555 g. 73%) as a white powder: m.p. 180°-181° C.; partial NMR (250 MHz, DMSO-d6): 1.17(m,2H); 1.4-1.8 (m,6H); 2.25(m,3H); 3.70(s,3H, NMe): 3.82(s,3H, OMe): 3.92(s,3H, OMe); 3.97(s,2H, ArCH2): 9.62(br s,1H, NH).

Workup

  1. extractionthe separated aqueous layer extracted with dichloromethane (3×25 ml.)
  2. washthe combined organic extracts washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-be459c70cddb486ea2c2771f635785aa
Source dataset
uspto-grants-1989_08
Patent number
US04859692

Reaction notes

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