Nitrogen → HCID 17984585, compound

HRID 1181064Notes

Reaction equation

C([O:5][C:6](=[O:39])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:31][NH:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])(C)(C)C.N#N.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[NH2:63][N:64]1[CH2:69][CH2:68][O:67][CH2:66][CH2:65]1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:36]([O:35][C:33]([NH:32][CH2:31][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([NH:63][N:64]4[CH2:69][CH2:68][O:67][CH2:66][CH2:65]4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:5])=[O:39])=[O:34])([CH3:37])[CH3:38]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3-[4-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (120 mg, 0.200 mmol) in toluene (2.0 mL) in a sealed tube under a flow of N2 was treated Pd2(dba)3 (10 mg), 2-(di-t-butylphosphino)biphenyl (10 mg), N-aminomorpholine (29 mg, 0.28 mmol), and sodium t-butoxide (38 mg, 0.40 mmol). The tube was sealed and heated at 100° C. for 60 min. The mixture was cooled and purified using silica gel chromatography (5-10% MeOH/EtOAc) to yield the title compound directly (22 mg, 21%): MS (ESI) m/z 567.3 (M+H)+.

Workup

customThe tube was sealed
temperatureThe mixture was cooled
custompurified

Sources & evidence

ORD record: ord-13df3926006b4bff9015548197182d57
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282501B2

Reaction notes

Loading…