Dimethylformamide → 2-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6), 7-dien-10-yl}-4-fluoro-N-methylbenzamide

HRID 519398Notes

Reaction equation

HRID 519398 reaction equation
[CH3:1][N:2](C=O)C.[Br:6][C:7]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([N:17]2[CH2:28][CH2:27][N:26]3[C:19](=[CH:20][C:21]4[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24][C:25]=43)[C:18]2=[O:31])[C:8]=1[C:9]([OH:11])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.Cl>CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[Br:6][C:7]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([N:17]2[CH2:28][CH2:27][N:26]3[C:19](=[CH:20][C:21]4[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24][C:25]=43)[C:18]2=[O:31])[C:8]=1[C:9]([NH:2][CH3:1])=[O:11]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6364545Methylamine hydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866837752-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-fluorobenzoic Acid

Product 1

HCID 866837762-Bromo-6-{4,4-dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6), 7-dien-10-yl}-4-fluoro-N-methylbenzamideYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

A 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with DMF (8 mL), 129a (160 mg, 0.38 mmol), HATU (505 mg, 1.33 mmol), DMAP (46 mg, 0.38 mmol), and triethylamine (1.0 mL). The mixture was heated at 25° C. for 0.5 h. Then MeNH2.HCl (266 mg, 3.8 mmol) was added and resulting mixture was stirred at 25° C. for 2.5 h. After this time the reaction was cooled to room temperature. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-TLC developing with 1:20 methanol/dichloromethane to afford 129b (116 mg, 70%) as a black solid. MS-ESI: [M+H]+ 434.0

Workup

  1. customA 25-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customresulting mixture
  3. temperatureAfter this time the reaction was cooled to room temperature
  4. filtrationIt was then filtered
  5. customthe filtrate was evaporated under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-07b16d09e6da45578730e7bc7d7452c1
Source dataset
uspto-grants-2015_08
Patent number
US09115152B2

Reaction notes

Loading…