Methanol → HCID 67521110, compound

HRID 1926290Notes

Reaction equation

HRID 1926290 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5].[CH3:11][O:12][CH:13]([O:18][CH3:19])[C:14](OC)=[O:15].C(N(CC)CC)C.CO>CCOC(C)=O>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:5][C:14](=[O:15])[CH:13]([O:18][CH3:19])[O:12][CH3:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 50998690(2-Chloro-3-fluorophenyl)methanamine

Product 1

HCID 67521110HCID 67521110, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-3-fluorobenzylamine (575 mg, 3.53 mmol), methyl dimethoxyacetate (512 mg, 3.78 mmol), triethylamine (0.62 mL, 4.4 mmol) and MeOH (1 mL, 20 mmol) in a sealed tube was heated at 80° C. for 20 h. After cooling to rt, the mixture was diluted with EtOAc (40 ml), washed with HCl (2N, 2×30 ml), water (2×30 ml), brine (30 ml), dried over MgSO4, filtered, and concentrate vacuo to give the title compound as a brown oil. 1H NMR (400 MHz, CDCl3): δ=3.40 (s, 6H), 4.59 (d, J=6.0 Hz, 2H), 4.74 (s, 1H), 6.99 (brs, 1H), 7.07-7.12 (m, 1H), 7.17-7.25 (m, 2H). MS(ES+): m/z=262.06/264.04 (100/62) [MH+]. HPLC: tR=2.91 min (ZQ3, polar—5 min).

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with HCl (2N, 2×30 ml), water (2×30 ml), brine (30 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrate vacuo

Sources & evidence

ORD record
ord-e438260508f74ff1bf5eb9f384b78f62
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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