2-amino-N-(4-tert-butylphenyl)benzamide → HCID 59017446, compound

HRID 969688Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-amino-N-(4-tert-butyl-phenyl)-benzamide (Step A, 163 mg, 0.61 mmol), 2-chloro-[1,7]naphthyridine (100 mg, 0.61 mmol), Pd2(dba)3 (6.0 mg, 0.006 mmol), 2-dicyclohexyl phosphino-2′-(N-N-dimethyamino)biphenyl (6.0 mg, 0.015 mmol), and LiN(TMS)2 (1 M solution in THF, 2.3 mL) was heated at 80° C. for 12 h in a sealed tube. The mixture was concentrated in vacuo and the crude material was purified with flash chromatography (SiO2, 20% EtOAc/hexane) and crystallization from EtOH to give the desired compound. MS (ES+): 397.0 (M+H)+. Calc'd for C25H24N4O-396.48.

Workup

concentrationThe mixture was concentrated in vacuo
customthe crude material was purified with flash chromatography (SiO2, 20% EtOAc/hexane) and crystallization from EtOH

Sources & evidence

ORD record: ord-6e5e5080d11a46ce9d0993eba20b20d5
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07307088B2

Reaction notes

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