Methyl 6-aminonicotinate → HCID 59560121, compound

HRID 1643558Notes

Reaction equation

HRID 1643558 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[N:6][CH:5]=1.C[O:13][C:14]([C:16]1[CH:26]=[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]2[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=2[CH:17]=1)=O>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:14]([C:16]2[CH:26]=[C:25]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])[C:19]3[CH2:20][C:21]([CH3:24])([CH3:23])[O:22][C:18]=3[CH:17]=2)=[O:13])=[N:6][CH:5]=1

Participants

3

Reactant 2

HCID 737487Methyl 6-aminonicotinateHCID 59559973HCID 59559973, compound

Product 1

HCID 59560121HCID 59560121, compound

Procedure

The title compound was prepared in a similar manner as described for Example 1, from 6-aminonicotinic acid methyl ester (1.0 g, 6.57 mmol) and 4-isobutoxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (14a) (185 mg, 0.66 mmol). Purification by column chromatography eluting with 15-25% EtOAc in hexane gave a pale yellow solid (127 mg, 48% yield). 1H NMR (400 MHz, CDCl3) δ 8.93 (d, J=1.52 Hz, 1 H) 8.69 (s, 1 H) 8.42-8.48 (m, 1 H) 8.35 (dd, J=8.72, 2.15 Hz, 1 H) 6.96 (s, 1 H) 6.87 (s, 1H) 3.95 (s, 3 H) 3.82 (d, J=6.32 Hz, 2 H) 3.01 (s, 2 H) 2.06-2.14 (m, J=13.33, 6.60, 6.60 Hz, 1 H) 1.51 (s, 6 H) 1.04 (d, J=6.82 Hz, 6 H); LCMS for C22H26N2O5 m/z 399.10 (M+H+).

Workup

  1. customPurification by column chromatography
  2. washeluting with 15-25% EtOAc in hexane

Sources & evidence

ORD record
ord-418b079ab7004dca8d463cff90494fcd
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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