Methylamine → HCID 89438439, compound

HRID 2203380Notes

Reaction equation

HRID 2203380 reaction equation
Br[C:2]1[C:3]2[C:29]([CH3:36])([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:28](=[O:37])[NH:27][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=3)[N:10]([CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[N:9]=2)[N:7]=1.[CH3:38][NH2:39]>C1COCC1>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16]([C:8]([C:6]3[N:7]=[C:2]([NH:39][CH3:38])[C:3]4[C:29]([CH3:36])([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:28](=[O:37])[NH:27][C:4]=4[N:5]=3)=[N:9][N:10]2[CH2:18][CH2:19][C:20]([F:26])([F:25])[C:21]([F:24])([F:22])[F:23])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89438408HCID 89438408, compound

Product 1

HCID 89438439HCID 89438439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from Step A above (35 mg, 0.058 mmol), methylamine (0.058 mL, 0.117 mmol, 2M in THF) and THF (0.5 mL) were stirred in a sealed tube at 50° C. for 1.5 h, then at 65° C. overnight. The reaction mixture was subjected to microwave irradiation at 150° C. for 2 h, The reaction mixture was partitioned between brine and EtOAc. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC to afford the indicated product, as a solid. 1H NMR (500 MHz, CD3OD): δ 8.64 (d, J=8.7 Hz, 1H); 7.77 (d, J=1.6 Hz, 1H); 7.38-7.31 (m, 4H); 7.32-7.28 (m, 2H); 4.82 (d, 7.1 Hz, 2H); 3.07 (s, 3H); 3.00-2.88 (m, 2H); 1.88 (s, 3H). m/z=551.0 (WE).

Workup

  1. customat 65° C.
  2. customovernight
  3. customirradiation at 150° C. for 2 h
  4. customThe reaction mixture was partitioned between brine and EtOAc
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by reverse phase HPLC
  9. customto afford the indicated product

Sources & evidence

ORD record
ord-f646e977b04044b99256bfc135611e61
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

Loading…