Isoamylamine → HCID 67316960, compound

HRID 1014079Notes

Reaction equation

[C:1]1(=[O:27])[N:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]2[C:14]([C:19](O)=[O:20])=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4](=[O:22])[C:3]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:2]12.[CH2:28]([NH2:33])[CH2:29][CH:30]([CH3:32])[CH3:31].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>>[CH2:28]([NH:33][C:19]([C:14]1[C:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]2[C:4](=[O:22])[C:3]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:2]3[C:1]2=[O:27])=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:20])[CH2:29][CH:30]([CH3:32])[CH3:31]

Participants

Reactant 4

HCID 7894Isoamylamine

HCID 12734Diisopropylcarbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 142585712'-Phthalimidomethylbiphenyl-2-carboxylic acid

Product 1

HCID 67316960HCID 67316960, compound

Procedure

From 3 g (8.4 mmol) of 2′-phthalimidomethylbiphenyl-2-carboxylic acid (precursor 2), by reaction with isopentylamine in the presence of HOBT and DIC, 3.2 g of 2′-phthalimidomethylbiphenyl-2-carboxylic acid isopentylamide were obtained; m.p. 169° C. The product was dissolved in 100 ml of methanol and treated with 5 ml of hydrazine hydrate. After stirring at 40° C. for 1 h, the cooled reaction mixture was filtered. The filtrate was concentrated and the residue was taken up in methylene chloride. After washing with water, drying and concentrating, 1.8 g of 2′-aminomethylbiphenyl-2-carboxylic acid isopentylamide were obtained.

Sources & evidence

ORD record: ord-f22d601219814ccd8cada52d12bf602e
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07982045B2

Reaction notes

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