Methylamine → HCID 60198719, compound

HRID 2279544Notes

Reaction equation

HRID 2279544 reaction equation
CS(O[CH2:6][CH2:7][CH:8]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([F:33])[CH:27]=1)[NH:9][C:10]([N:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[N:17][C:16]([NH:22][CH:23]([CH3:25])[CH3:24])=[N:15][C:14]=2[CH2:13]1)=[O:11])(=O)=O.[CH3:34][NH2:35]>C1COCC1>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([CH:8]([NH:9][C:10]([N:12]2[CH2:21][CH2:20][C:19]3[CH:18]=[N:17][C:16]([NH:22][CH:23]([CH3:25])[CH3:24])=[N:15][C:14]=3[CH2:13]2)=[O:11])[CH2:7][CH2:6][NH:35][CH3:34])=[CH:27][C:28]=1[F:33]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86705531HCID 86705531, compound

Product 1

HCID 60198719HCID 60198719, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 310 (0.059 g, 0.12 mmol) and THF (3 mL) was added methylamine (0.092 g, 1.2 mmol, 40% aqueous solution) and the reaction was stirred at 45° C. for 1 h. The solution was concentrated, poured into water and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH (500:30) to afford 3 mg (5.8%) of I-78: MS m/z (APCI-pos) M+1=435.

Workup

  1. concentrationThe solution was concentrated
  2. additionpoured into water
  3. extractionextracted with DCM
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with DCM/MeOH (500:30)
  9. customto afford 3 mg (5.8%) of I-78: MS m/z (APCI-pos) M+1=435

Sources & evidence

ORD record
ord-aaede4eac4854d02b242311ccb35bc27
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

Loading…