Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)- → HCID 19426877, compound

HRID 741702Notes

Reaction equation

HRID 741702 reaction equation
[I:1][C:2]1[NH:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH2:6].[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1.CC1NC2C=CC(OC)=CC=2C=1CCNC(C)=O>C1COCC1>[I:1][C:2]1[NH:13][C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[C:3]=1[CH2:4][CH2:5][NH:6][C:19]([CH:16]1[CH2:18][CH2:17]1)=[O:20]

Participants

5

Reactant 3

HCID 50279Acetamide, N-(2-(5-methoxy-2-methyl-3-indolyl)ethyl)-HCID 77637Cyclopropanecarbonyl chlorideHCID 21791229HCID 21791229, compound

Product 1

HCID 19426877HCID 19426877, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-iodo-5-methoxytryptamine (0.316 g, 1 mmol), in THF (3 mL) and TEA (0.14 mL) was acylated with cyclopropanecarbonyl chloride (0.09 mL) at room temperature for 1.5 h using the procedure described for 4a. The desired product 4m was obtained as amorphous solid (0.34 g, 89% yield), IR νmax :3450, 3300, 1650. 1H NMR: 0.71(m, 2H, CH2cyclopropyl), 0.96(m, 2H, CH2cyclopropyl), 1.21(m, 1H, cyclopropyl-CH), 2.90(t, 2H, β -CH2), 3.55(q, 2H, α-CH2), 3.85(s, 3H, OCH3), 5.62(br s, 1H, NH), 6.78-7.27(m, 3Harom), 8.21(br s, 1H, NHindole).

Sources & evidence

ORD record
ord-f0668dbd3e4c463bb06cd13f881d0f07
Source dataset
uspto-grants-1996_09
Patent number
US05552428

Reaction notes

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