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

HRID 887679Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:12][C:13]1[CH:31]=[CH:30][CH:29]=[CH:28][C:14]=1[C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=1)=[O:16].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[Li]N([Si](C)(C)C)[Si](C)(C)C>C1COCC1.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:24]([C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:15](=[O:16])[C:14]2[CH:28]=[CH:29][CH:30]=[CH:31][C:13]=2[NH:12][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][N:6]=[CH:7][CH:8]=3)[N:3]=2)=[CH:19][CH:20]=1)([CH3:27])([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 70 °C

Procedure

2-Chloro-[1,7]naphthyridine (100 mg, 0.61 mmol), 2-amino-N-(4-tert-butyl-phenyl)-benzamide (164 mg, 0.61 mmol), Pd2(dba)3 (6 mg, 0.006 mmol), (2′-Dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (6 mg, 0.015 mmol), and 1M solution of LiN(TMS)2 in THF (1.83 mL), 1.83 mmol) were added to a reaction vessel. The vessel was sealed and the reaction was stirred at 70° C. for 24 h. The mixture was cooled to RT, and solvent was removed under vacuum. The crude was purified by flash column chromatography (gradient, 0 to 100% EtoAC/Hexane) to give the product as tan solid. MS (ES−): 397.0 (M+H)+. Calc'd for C25H24N4O—396.20.

Workup

customThe vessel was sealed
temperatureThe mixture was cooled to RT
customsolvent was removed under vacuum
customThe crude was purified by flash column chromatography (gradient, 0 to 100% EtoAC/Hexane)

Sources & evidence

ORD record: ord-12699cf13e09485098d1ee466670c4d0
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247430B2

Reaction notes

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