Trifluoroacetic acid → 8-Chloro-4-[3-(2-methyl-oxazol-4-yl)-phenyl]-7-(methyl-propyl-amino)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

HRID 1265928Notes

Reaction equation

HRID 1265928 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])[C:11]([Cl:19])=[CH:10][C:9]=1[NH2:20])(C)(C)C.C(O[C:27](=[O:43])[CH2:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]2[N:37]=[C:38]([CH3:41])[O:39][CH:40]=2)[CH:31]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:19][C:11]1[C:12]([N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:13][C:8]2[N:7]=[C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]4[N:37]=[C:38]([CH3:41])[O:39][CH:40]=4)[CH:31]=3)[CH2:28][C:27](=[O:43])[NH:20][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69688379Carbamic acid,[2-amino-4-chloro-5-(methylpropylamino)phenyl]-,1,1-dimethylethyl esterHCID 696892093-Oxo-3-[3-(2-methyl-oxazol-4-yl)-phenyl]-propionic acid tert-butyl ester

Product 1

HCID 186134428-Chloro-4-[3-(2-methyl-oxazol-4-yl)-phenyl]-7-(methyl-propyl-amino)-1,3-dihydro-benzo[b][1,4]diazepin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from [2-amino-4-chloro-5-(methyl-propyl-amino)-phenyl]-carbamic acid tert-butyl ester (0.16 g) (Example J8) and 3-oxo-3-[3-(2-methyl-oxazol-4-yl)-phenyl]-propionic acid tert-butyl ester (0.17 g) (Example K29) according to the general procedure M. The obtained material was deprotected and cyclized by treatment with TFA in CH2Cl2 according to the general procedure N. Obtained as a yellow solid (0.07 g).

Sources & evidence

ORD record
ord-bf5bbb09caa14875ae728843771287ad
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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