Tert-butyl (4,4,4-trifluoro-1-hydroxybutan-2-yl)carbamate → Tert-butyl (1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4,4,4-trifluorobutan-2-yl)carbamate

HRID 1398462Notes

Reaction equation

HRID 1398462 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.[F:19][C:20]([F:34])([F:33])[CH2:21][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:23][OH:24]>CCOCC>[CH3:15][C:10]1[N:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[C:8](=[O:16])[N:7]([CH3:17])[C:6]1[CH:18]=[C:2]([O:24][CH2:23][CH:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH2:21][C:20]([F:34])([F:33])[F:19])[CH:3]=[CH:4][C:5]2=1

Participants

4

Reactant 2

HCID 23237059Tert-butyl (4,4,4-trifluoro-1-hydroxybutan-2-yl)carbamateHCID 867103378-Chloro-4,6-dimethyl-5H,6H-benzo[c]2,7-naphthyridin-5-one

Product 1

HCID 86710435Tert-butyl (1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4,4,4-trifluorobutan-2-yl)carbamateYield 49%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

8-Chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one and tert-butyl (4,4,4-trifluoro-1-hydroxybutan-2-yl)carbamate were used for ether synthesis as described in Example 16, Part H to afford tert-butyl (1-((4,6-dimethyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-4,4,4-trifluorobutan-2-yl)carbamate (0.22 g, 0.473 mmol, 49% yield) as a semi-solid. LC/MS (ESI) m/e 466.2 [(M+H)+, calcd for C23H27F3N3O4 466.2]; LC/MS retention time (method D): tR=0.82 min.

Sources & evidence

ORD record
ord-c97d0302b46e443ab0fe339e2b29491b
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

Loading…