HCID 86700230, compound → (S)-ethyl 2-(2-(3-amino-4-(methylamino)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

HRID 879426Notes

Reaction equation

HRID 879426 reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:31]([CH3:32])=[CH:30][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][CH3:26])=[C:21]([N+:27]([O-])=O)[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]>CCO.CCOC(C)=O.[Pt]>[NH2:27][C:21]1[CH:20]=[C:19]([C:17]2[S:18][C:14]3[C:13]([C:33]4[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=4)=[C:12]([C@H:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:31]([CH3:32])=[CH:30][C:15]=3[N:16]=2)[CH:24]=[CH:23][C:22]=1[NH:25][CH3:26]

Participants

5

Reactant 1

HCID 86700230HCID 86700230, compound

Product 1

HCID 86700231(S)-ethyl 2-(2-(3-amino-4-(methylamino)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(4-(methylamino)-3-nitrophenyl)benzo[d]thiazol-6-yl)acetate (510 mg) in EtOH (4 mL) and EtOAc (2 mL) was added 5% Pt/C (150 mg). The reaction mixture was flushed with hydrogen gas and stirred under hydrogen atmosphere (using a balloon) for 1.5 h. The mixture was filtered through celite and concentrated in vacuo and (S)-ethyl 2-(2-(3-amino-4-(methylamino)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate was used without further purification. LCMS-ESI+: calc'd for C29H33ClN3O3S: 538.2 (M+H+); Found: 538.2 (M+H+).

Workup

  1. customThe reaction mixture was flushed with hydrogen gas
  2. customfor 1.5 h
  3. filtrationThe mixture was filtered through celite and
  4. concentrationconcentrated in vacuo and (S)-ethyl 2-(2-(3-amino-4-(methylamino)phenyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate
  5. customwas used without further purification

Sources & evidence

ORD record
ord-19519786ea0e4f369001f12a86b849c6
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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