Benzoic acid, 2-amino-3-chloro-, methyl ester → Methyl 3-chloro-2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)benzoate

HRID 20649Notes

Reaction equation

HRID 20649 reaction equation
[NH2:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:14]1[C:23]2[C:18](=[C:19]([O:26][CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[O:17][C:16](=[O:32])[CH:15]=1>>[Cl:12][C:11]1[C:2]([NH:1][C:14]2[C:23]3[C:18](=[C:19]([O:26][CH:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[O:17][C:16](=[O:32])[CH:15]=2)=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

3

Reactant 2

HCID 11030511Benzoic acid, 2-amino-3-chloro-, methyl esterHCID 771747944-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

Product 1

HCID 24849519Methyl 3-chloro-2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)benzoate

Procedure

The title compound was prepared from methyl 2-amino-3-chlorobenzoate and 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one following the procedure outlined in Example 16 (30 min r×n time). 1H NMR (400 MHz, DMSO-d6): δ 9.29 (s, 1H), 7.92 (m, 3H), 7.59 (t, 1H), 7.19 (d, 1H), 4.85 (m, 1H), 4.40 (s, 1H), 3.92 (s, 3H), 3.70 (s, 3H), 1.90-1.50 (m, 8H); MS (ESI): 443.9.

Workup

  1. customoutlined in Example 16 (30 min r×n time)

Sources & evidence

ORD record
ord-8a754a9c072f48ac859b112822dca216
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Reaction notes

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