Methylamine → HCID 86679015, compound

HRID 2203377Notes

Reaction equation

HRID 2203377 reaction equation
Br[C:2]1[C:3]2[C:28]([CH3:35])([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:27](=[O:36])[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.[CH3:37][NH2:38]>C1COCC1>[CH3:35][C:28]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:3]2[C:2]([NH:38][CH3:37])=[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:25])([F:24])[C:20]([F:21])([F:23])[F:22])[N:9]=3)=[N:5][C:4]=2[NH:26][C:27]1=[O:36]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86679016HCID 86679016, compound

Product 1

HCID 86679015HCID 86679015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from Step A above (100 mg, 0.176 mmol), methylamine (0.881 mL, 1.763 mmo, 2 M in THF) and THF (2 mL) were sealed in a microwave tube and subject to microwave irradiation at 140° 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 give the title product, as a solid. 1H NMR (500 MHz, CD3OD) δ 9.01 (dd, J=8.1, 1.6 Hz, 1H); 8.6 (dd, J=4.5, 1.6 Hz, 1H); 7.39-7.32 (m, 5H); 7.32-7.27 (m, 1H); 4.96 (t, J=7.3 Hz, 3H); 3.07 (s, 3H); 3.05-2.91 (m, 2H); 1.88 (s, 3H). m/z=518.1 (M+H).

Workup

  1. customsubject to microwave irradiation at 140° C. for 2 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. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-d6a968a3c80341df92246bef4611c7d7
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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