1-Butanol → HCID 44159934, compound

HRID 517845Notes

Reaction equation

HRID 517845 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]3[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18][C:5]=3[C:4]=2[CH:3]=1.CCN=C=NCCCN(C)C.[CH2:31](O)[CH2:32][CH2:33][CH3:34]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH2:11][C:12]([O:14][CH2:31][CH2:32][CH2:33][CH3:34])=[O:13])[C:6]3[CH2:15][CH2:16][N:17]([CH3:19])[CH2:18][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59161636HCID 59161636, compound

Product 1

HCID 44159934HCID 44159934, compound

Procedure

2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetic acid was mixed with EDCI and 1-butanol and the reaction mixture was stirred for 16 h to obtain butyl 2-(8-chloro-1,2,3,4-tetrahydro-2-methylpyrido[4,3-b]indol-5-yl)acetate after purification on neutral alumina chromatography eluting with methanol-dichloromethane gradient. The free base was converted into its oxalate salt by treatment of oxalic acid (1 equiv) in anhydrous THF.

Sources & evidence

ORD record
ord-969ab640de634c1e920c78ca6ba4a0ae
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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