(R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate → (R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-one

HRID 1853705Notes

Reaction equation

HRID 1853705 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[NH:9][C:8](=[O:13])[C:7]3[S:14][CH:15]=[CH:16][C:6]=3[C:5]=2[C:4]=1[C:17]1[CH:22]=[CH:21][C:20]([C@@H:23]([CH3:33])[CH2:24][NH:25]C(=O)OC(C)(C)C)=[CH:19][CH:18]=1>C(O)(C(F)(F)F)=O>[NH2:25][CH2:24][C@@H:23]([C:20]1[CH:19]=[CH:18][C:17]([C:4]2[C:5]3[C:6]4[CH:16]=[CH:15][S:14][C:7]=4[C:8](=[O:13])[NH:9][C:10]=3[CH:11]=[CH:12][C:3]=2[O:2][CH3:1])=[CH:22][CH:21]=1)[CH3:33]

Participants

3

Reactant 1

HCID 67448651(R)-tert-Butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate

Product 1

HCID 67448915(R)-9-(4-(1-Aminopropan-2-yl)phenyl)-8-methoxythieno[2,3-c]quinolin-4(5H)-oneYield 81.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Following General Procedure C (R)-tert-butyl 2-(4-(8-methoxy-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)propylcarbamate (2.5 g, 5.4 mmol) was reacted with TFA (10 mL) to afford the desired product (1.6 g, 81%) as an off-white solid: ESI MS m/z 365 [C21H20N2O2S+H]+

Sources & evidence

ORD record
ord-b578685893d24d9ea19e51e9b351095b
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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