Methylamine → HCID 86679018, compound

HRID 2203378Notes

Reaction equation

HRID 2203378 reaction equation
Br[C:2]1[C:3]2[C:28]([CH3:34])([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:27](=[O:35])[NH:26][C:4]=2[N:5]=[C:6]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][C:19]([F:25])([F:24])[C:20]([F:23])([F:22])[F:21])[N:9]=2)[N:7]=1.[CH3:36][NH2:37]>C1COCC1>[CH3:34][C:28]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:3]2[C:2]([NH:37][CH3:36])=[N:7][C:6]([C:8]3[C:16]4[C:11](=[N:12][CH:13]=[CH:14][CH:15]=4)[N:10]([CH2:17][CH2:18][C:19]([F:24])([F:25])[C:20]([F:23])([F:22])[F:21])[N:9]=3)=[N:5][C:4]=2[NH:26][C:27]1=[O:35]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 89157517HCID 89157517, compound

Product 1

HCID 86679018HCID 86679018, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from Step A above (190 mg, 0.337 mmol), methylamine (2M in THF) (0.843 mL, 1.687 mmol) and THF (2 mL) were sealed in a microwave tube and subjected to microwave irradiation at 150° C. for 3 h. The reaction mixture was partitioned between brine and EtOAc. The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford a dark solid. The residue was purified by reverse phase preparative HPLC to give the title product, as a solid. 1H NMR (500 MHz, DMSO-d6): δ 11.35 (s, 1H); 8.87 (d, J=8.1 Hz, 1H); 8.64-8.62 (m, 1H); 7.39 (dd, J=8.1, 4.5 Hz, 1H); 6.61 (d, J=4.9 Hz, 1H); 4.88 (t, J=6.8 Hz, 2H); 4.12-4.07 (m, 2H); 3.04-2.90 (m, 5H); 1.61 (s, 3H); 1.09 (t, J=7.1 Hz, 3H). m/z=514.1 (M+H).

Workup

  1. customirradiation at 150° C. for 3 h
  2. customThe reaction mixture was partitioned between brine and EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a dark solid
  7. customThe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-037855ce2cdb4813b32055c501b8c7b6
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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