Diisopropylethylamine → N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(benzo[d]oxazol-2-yl)nicotinamide

HRID 1400238Notes

Reaction equation

HRID 1400238 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=O.[NH2:19][CH:20]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:21]([OH:25])[C:22]([NH2:24])=[O:23].CCN(C(C)C)C(C)C>>[NH2:24][C:22](=[O:23])[CH:21]([OH:25])[CH:20]([NH:19][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[N:18][C:10]=1[C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1)[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 138823553-Amino-2-hydroxy-4-phenylbutanamideHCID 675405322-(Benzo[d]oxazol-2-yl)nicotinic acid

Product 1

HCID 67540448N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(benzo[d]oxazol-2-yl)nicotinamideYield 85.9%

Procedure

Coupling of 2-(benzo[d]oxazol-2-yl)nicotinic acid (190 mg, 0.791 mmol) and 3-amino-2-hydroxy-4-phenylbutanamide (169 mg, 0.780 mmol) was performed by analogy to the method described for example 1.2 using DIPEA instead of triethylamine. The reaction yielded 279 mg of the title compound; ESI-MS [M+H+]=417.1.

Sources & evidence

ORD record
ord-c2568ba881e84bd0b0f0c5755b7caae1
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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