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

HRID 1265916Notes

Reaction equation

HRID 1265916 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:50])[CH2:28][C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([C:36]2[O:37][CH:38]=[C:39]([CH2:41][O:42]C3CCCCO3)[N: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[O:37][CH:38]=[C:39]([CH2:41][OH:42])[N:40]=4)[CH:31]=3)[CH2:28][C:27](=[O:50])[NH:20][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 696880223-Oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-2-yl]-phenyl]-propionic acid tert-butyl esterHCID 69688379Carbamic acid,[2-amino-4-chloro-5-(methylpropylamino)phenyl]-,1,1-dimethylethyl ester

Product 1

HCID 101380668-Chloro-4-[3-(4-hydroxymethyl-oxazol-2-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-[4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-2-yl]-phenyl]-propionic acid tert-butyl ester (0.22 g) (Example K11) 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 (0.10 g).

Sources & evidence

ORD record
ord-a242521e9c1342dcbe7ab12a1184bad4
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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