Trifluoroacetic acid → 5-{2-[(3-{[(Benzylamino)carbonyl]amino}benzyl)amino]-2-oxoethyl}-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl acetate

HRID 2213157Notes

Reaction equation

HRID 2213157 reaction equation
C(OC(=O)C[CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[N:11]([CH2:20][C:21]([O-])=[O:22])[C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2)(C)(C)C.[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]([NH:37][C:38]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:39])[CH:34]=[CH:35][CH:36]=1.[C:48]([OH:54])([C:50](F)(F)F)=[O:49]>C(OC)(C)(C)C.CO>[C:48]([O:54][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C:12](=[O:19])[N:11]([CH2:20][C:21]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([NH:37][C:38]([NH:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:39])[CH:32]=2)=[O:22])[C:10]2[CH:24]=[CH:25][CH:26]=[CH:27][C:9]1=2)(=[O:49])[CH3:50]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21955411N-[3-(Aminomethyl)phenyl]-N'-benzylureaHCID 2195546111-(2-tert-butoxy-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-5-ylacetate

Product 1

HCID 219555135-{2-[(3-{[(Benzylamino)carbonyl]amino}benzyl)amino]-2-oxoethyl}-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-11-yl acetate

Reagents, catalysts & solvents 1

HCID 22277986MTBE methanolSolvent

Procedure

Coupling of 11-(2-tert-butoxy-2-oxoethyl)-6-oxo-6,11-dihydro-5H-dibenzo[b,e]azepin-5-yl acetate (66) with (3-{[(benzylamino)-carbonyl]amino}phenyl)methanamine (hydrochloride) (41), TFA cleavage and stirring of the resulting crude product with methyl tert-butyl ether/CH3OH 19:1 afforded 0.61 g of slightly brownish solids; ESI-MS [M+H+]=563.25.

Workup

  1. customafforded 0.61 g of slightly brownish solids

Sources & evidence

ORD record
ord-1bce2b55572f4327be5a30c3f8323560
Source dataset
uspto-grants-2006_09
Patent number
US07105508B1

Reaction notes

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