Ammonia → HCID 86710407, compound

HRID 1398418Notes

Reaction equation

HRID 1398418 reaction equation
II.[F:3][C:4]([F:37])([F:36])[CH2:5][CH2:6][CH:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:8][O:9][C:10]1[C:11]([CH:26]=O)=[CH:12][C:13]2[C:22]3[C:17](=[CH:18][N:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([CH3:24])[C:14]=2[CH:25]=1.[NH3:38].[O-]S([O-])(=S)=O.[Na+].[Na+]>O1CCCC1>[C:26]([C:11]1[C:10]([O:9][CH2:8][CH:7]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:32])[CH3:34])[CH2:6][CH2:5][C:4]([F:36])([F:37])[F:3])=[CH:25][C:14]2[N:15]([CH3:24])[C:16](=[O:23])[C:17]3[C:22]([C:13]=2[CH:12]=1)=[CH:21][CH:20]=[N:19][CH:18]=3)#[N:38]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 807IodineHCID 24477Sodium ThiosulfateHCID 86710408HCID 86710408, compound

Product 1

HCID 86710407HCID 86710407, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodine (0.047 g, 0.184 mmol) was added to a stirred solution of tert-butyl (5,5,5-trifluoro-1-((9-formyl-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)pentan-2-yl)carbamate (0.165 g, 0.167 mmol) in aqueous ammonia (4 mL, 48.1 mmol) and tetrahydrofuran (6 mL) at room temperature. The dark solution became light gray after stirring for 3 h, an indication that the reaction was complete. The reaction mixture was charged with aqueous Na2S2O3 (25 mL of 5% solution) and extracted with ethyl acetate (3×30 mL). The combined the organic layers were dried over sodium sulphate and concentrated under reduced pressure to afford tert-butyl (1-((9-cyano-6-methyl-5-oxo-5,6 dihydrobenzo[c][2,7]naphthyridin-8-yl)oxy)-5,5,5-trifluoropentan-2-yl)carbamate (0.14 g, 0.143 mmol, 85% crude yield) as a pale yellow solid. The material was carried forward without further purification. LC/MS (ESI) m/e 491.5 (M+H)+, calcd for C24H26F3N4O4, 491.2]; LC/MS retention time (method D): tR=0.87 min.

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. dry with materialwere dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2471d15760c341d0976c0323ee1b1b50
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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