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

HRID 1265929Notes

Reaction equation

HRID 1265929 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]([CH3:19])=[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[S: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>[OH:42][CH2:41][C:39]1[N:40]=[C:36]([C:32]2[CH:31]=[C:30]([C:29]3[CH2:28][C:27](=[O:50])[NH:20][C:9]4[CH:10]=[C:11]([CH3:19])[C:12]([N:14]([CH3:18])[CH2:15][CH2:16][CH3:17])=[CH:13][C:8]=4[N:7]=3)[CH:35]=[CH:34][CH:33]=2)[S:37][CH:38]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69688441Carbamic acid,[2-amino-4-methyl-5-(methylpropylamino)phenyl]-,1,1-dimethylethyl esterHCID 696884923-Oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert-butyl ester

Product 1

HCID 186132614-[3-(4-Hydroxymethyl-thiazol-2-yl)-phenyl]-8-methyl-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-methyl-5-(methyl-propyl-amino)-phenyl]-carbamic acid tert-butyl ester (0.21 g) (Example J24) and 3-oxo-3-[3-[4-(tetrahydro-pyran-2-yloxymethyl)-thiazol-2-yl]-phenyl]-propionic acid tert-butyl ester (Example K27) (0.31 g) 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 (0.09 g).

Sources & evidence

ORD record
ord-f20139d650cc42e2889f6236c1ac80ef
Source dataset
uspto-grants-2003_04
Patent number
US06544985B2

Reaction notes

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