Isobutylamine → HCID 20767927, compound

HRID 1825146Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:13]([OH:15])=O)=[C:3]1[CH3:16].C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:27])[CH:24]([CH3:26])[CH3:25]>>[CH2:23]([NH:27][C:13]([C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[CH3:16])=[O:15])[CH:24]([CH3:26])[CH3:25]

Participants

Reactant 3

HCID 6558Isobutylamine

HCID 65578Oxalyl chloride

HCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 20767927HCID 20767927, compound

Procedure

This material was prepared from 1,2-dimethyl-6-methoxy-1H-indole-3-carboxylic acid 16c, oxalyl chloride and isobutylamine in a manner as previously described for example 16d. 1H NMR (300 MHz, CDCl3) δ 7.56 (1H, d, J=8.6 Hz), 6.85 (1H, dd, J=2.2, 8.6 Hz), 6.78 (1H, d, J=2.2 Hz), 3.87 (3H, s), 3.63 (3H, s), 3.32 (2H, m), 2.69 (3H, s), 1.93 (1H, m), 1.02 (3H, s), 1.00 (3H, s). LCMS (ESI+) [M+H]/z Calc'd 275. found 275.

Sources & evidence

ORD record: ord-60be3d0b7e814fd2a96b7a57b3c368ce
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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