Dimethyl 5-aminoisophthalate → HCID 70161367, compound

HRID 1018312Notes

Reaction equation

[CH2:1]([N:8]1[C:12]([CH2:13][CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:11]([C:21](O)=[O:22])[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][O:25][C:26](=[O:38])[C:27]1[CH:36]=[C:35]([NH2:37])[CH:34]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=1>>[CH3:33][O:32][C:30](=[O:31])[C:29]1[CH:34]=[C:35]([NH:37][C:21]([C:11]2[N:10]=[CH:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:12]=2[CH2:13][CH:14]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:22])[CH:36]=[C:27]([C:26]([O:25][CH3:24])=[O:38])[CH:28]=1

Participants

Reactant 2

HCID 66831Dimethyl 5-aminoisophthalate

HCID 18405564HCID 18405564, compound

Product 1

HCID 70161367HCID 70161367, compoundYield 20%

Procedure

The product of step b above (310 mg, 1.00 mmol) was reacted with 5-amino-isophthalic acid dimethyl ester (210 mg, 1.00 mmol) using essentially the same procedure as in Example 20, step d. The crude product was purified by flash column chromatography (silica, DCM/ethyl acetate 92:8) to afford colourless foam (110 mg, 20%). 1H NMR (300 MHz,CDCl3) 9.36 (1H, s), 8.53 (2H, s), 8.40 (1H, s), 7.35 (4H, m), 7.08 (2H, m), 5.12 (2H, s), 3.94 (6H, s), 1.90-1.22 (13H, m).

Workup

customThe crude product was purified by flash column chromatography (silica, DCM/ethyl acetate 92:8)

Sources & evidence

ORD record: ord-20a23d14f855404f91754e546b1fd371
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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