Isopropenyl chloroformate → Prop-1-en-2-yl(2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)phenyl)carbamate

HRID 715105Notes

Reaction equation

HRID 715105 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH3:30])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([N:19]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH3:20])[CH:13]=3)[CH:5]=[CH:6][C:7]=1[F:8].C([O-])(O)=O.[Na+].Cl[C:37]([O:39][C:40]([CH3:42])=[CH2:41])=[O:38]>CCOC(C)=O>[CH2:41]=[C:40]([O:39][C:37](=[O:38])[NH:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH3:30])=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([N:19]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH3:20])[CH:13]=3)[CH:5]=[CH:6][C:7]=1[F:8])[CH3:42]

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 516892Sodium BicarbonateHCID 898157773-(3-amino-4-fluorophenyl)-N-(4-methoxybenzyl)-N,2-dimethyl-1,6-naphthyridin-7-amine

Product 1

HCID 89827713Prop-1-en-2-yl(2-fluoro-5-(7-((4-methoxybenzyl)(methyl)amino)-2-methyl-1,6-naphthyridin-3-yl)phenyl)carbamateYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 3-(3-amino-4-fluorophenyl)-N-(4-methoxybenzyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (0.334 g, 0.830 mmol) in EtOAc (10 mL) with satd. NaHCO3 (10 mL), add isopropenyl chloroformate (0.100 mL, 0.913 mmol) and stir at RT for 2 h. Separate the layers, extract the aqueous layer with EtOAc (2×), dry the combined organics over MgSO4 and concentrate to dryness to afford the title compound (398 mg, 99%). MS (ESI) m/z: 487.2 (M+H+).

Workup

  1. customSeparate the layers
  2. extractionextract the aqueous layer with EtOAc (2×)
  3. dry with materialdry the combined organics over MgSO4
  4. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-0c440bdc877d4aa3bfc9aab5d32464ce
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

Loading…