Methylamine → HCID 89815338, compound

HRID 715100Notes

Reaction equation

HRID 715100 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[C:14]([F:21])=[CH:15][C:16]([F:20])=[C:17]([NH2:19])[CH:18]=3)[C:8]([CH3:12])=[N:9]2)=[CH:4][N:3]=1.[CH3:22][NH2:23]>CCOC(C)=O>[NH2:19][C:17]1[C:16]([F:20])=[CH:15][C:14]([F:21])=[C:13]([C:7]2[C:8]([CH3:12])=[N:9][C:10]3[C:5]([CH:6]=2)=[CH:4][N:3]=[C:2]([NH:23][CH3:22])[CH:11]=3)[CH:18]=1

Participants

4

Reactant 2

HCID 6329Methylamine3×HCID 89815720HCID 89815720, compound

Product 1

HCID 89815338HCID 89815338, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Heat a solution of 5-(7-chloro-2-methyl-1,6-naphthyridin-3-yl)-2,4-difluorobenzenamine (0.55 g, 1.799 mmol) in methylamine (33% in EtOH, 10 mL, 1.799 mmol) at 120° C. with microwave irradiation for 12 h. Add additional methylamine (33% in EtOH, 2 mL), heat the mixture at 120° C. for 12 h, add more methylamine (33% in EtOH, 2 mL) and irradiate at 120° C. for 15 h. Dilute the mixture with EtOAc, wash with satd. NaHCO3 (2×), dry and evaporated to yield the title compound (0.53 g, 98%). MS(ESI) m/z: 301.1 (M+H+).

Workup

  1. customwith microwave irradiation for 12 h
  2. customirradiate at 120° C. for 15 h
  3. washwash with satd
  4. dry with materialNaHCO3 (2×), dry
  5. customevaporated

Sources & evidence

ORD record
ord-4e85d30bec5c42d79689d9dd89bfdffa
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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