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

HRID 1265773Notes

Reaction equation

HRID 1265773 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:16])[CH3:15])[C:11]([Cl:17])=[CH:10][C:9]=1[NH2:18])(C)(C)C.C(O[C:25](=[O:48])[CH2:26][C:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34]2[O:35][CH:36]=[C:37]([CH2:39][O:40]C3CCCCO3)[N:38]=2)[CH:29]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:17][C:11]1[C:12]([N:14]([CH3:16])[CH3:15])=[CH:13][C:8]2[N:7]=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([C:34]4[O:35][CH:36]=[C:37]([CH2:39][OH:40])[N:38]=4)[CH:29]=3)[CH2:26][C:25](=[O:48])[NH:18][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 69688689(2-Amino-4-chloro-5-dimethylamino-phenyl)-carbamic acid tert.-butyl ester

Product 1

HCID 186132288-Chloro-7-dimethylamino-4-[3-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-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-dimethylamino-phenyl)-carbamic acid tert.-butyl ester (Example J2) (170 mg) and (RS)-3-oxo-3-{3-[4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-2-yl]-phenyl}-propionic acid tert-butyl ester (Example K11) (270 mg) 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 light yellow solid (110 mg).

Sources & evidence

ORD record
ord-16b3cdf15f324368a0afacea67468b82
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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