Benzoic Acid → HCID 86628609, compound

HRID 1919888Notes

Reaction equation

HRID 1919888 reaction equation
C([C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:8])=[CH:5][CH:4]=1)=O.COC1C=C(OC)C=CC=1[CH2:30][NH2:31].[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([N+:46]#[C-:47])=[CH:42][CH:41]=1.[C:48]([OH:56])(=O)[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C([OH:62])C(F)(F)F>>[C:48]([NH:31][CH:30]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:8])=[CH:24][CH:25]=1)[C:47]([NH:46][C:43]1[CH:44]=[CH:45][C:40]([O:39][CH3:38])=[CH:41][CH:42]=1)=[O:62])(=[O:56])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

6

Reactant 5

HCID 243Benzoic AcidHCID 64092,2,2-TrifluoroethanolHCID 4497651-isocyano-4-methoxybenzeneHCID 5972502,4-DimethoxybenzylamineHCID 22668143Tert-butyl {2-[(4-formylbenzoyl)amino]phenyl}carbamate

Product 1

HCID 86628609HCID 86628609, compound

Conditions

Temperature
50 °C

Procedure

The compound from Step A above (50 mg, 0.147 mmol), 2,4-dimethoxybenzylamine (26.5 mL, 0.176 mmol), 4-methoxyphenylisocyanide (19.6 mg, 0.147 mmol), and benzoic acid (17.9 mg, 0.147 mmol) were dissolved in 50 μL of trifluoroethanol (TFE) and heated at 50° C. for 3 h. The solution was purified by flash chromatography (12-100% EtOAc in hexanes) to give tert-butyl {2-[(4-{1-(benzoylamino)-2-[(4-methoxyphenyl)amino]-2-oxoethyl}benzoyl)amino]phenyl}carbamate, which was dissolved in 1 mL of CH2Cl2 and 1 mL of TFA was added. The solution was allowed to stir for 1 h, the solvents were evaporated and the residue was triturated twice with 5 mL of Et2O to give the desired product as a yellow powder. 1H NMR (600 MHz, CD3OD) δ 8.06 (d, J=8.2 Hz, 2H), 7.89 (d, J=7.3 Hz, 2H), 7.76 (d, J=8.5 Hz, 2H), 7.56 (t, J=7.4 Hz, 1H), 7.44-7.49 (m, 4H), 7.31-7.38 (m, 4H), 6.87 (d, J=7.1 Hz, 2H), 5.91 (s, 1H), 3.75 (s, 3H), MS cal'd 495 (MH+), exp 495 (MH+).

Workup

  1. customThe solution was purified by flash chromatography (12-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1933f9febd1047ec838da4dec6b8e76b
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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