Methylamine → HCID 10453217, compound

HRID 2293916Notes

Reaction equation

HRID 2293916 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.[CH3:21][NH2:22]>C1COCC1.O>[I:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[CH2:13][NH:12][C:4]1[N:3]=[C:2]([NH:22][CH3:21])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[CH3:11]

Participants

5

Reactant 2

HCID 6329Methylamine2×HCID 10340909HCID 10340909, compound

Product 1

HCID 10453217HCID 10453217, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of compound 6 (25 mg, 0.06 mmol) and 2M methylamine in THF (1 mL) and 40% methylamine in water (1 mL) was stirred for 14 h at 85° C. After removal of volatiles in vacuo, the residue was triturated with methanol-water, and the solid that formed was collected by suction filtration, washed with water (10 mL), and dried to give compound 11 (22 mg, 89.0%). 1H NMR (DMSO-d6) δ 2.76 (d, J=4.6 Hz, 3 H, NHCH3), 3.55 (s, 3 H, 9-CH3), 4.59 (br s, 2 H, CH2), 6.28 (br d, J=4.3 Hz, 1 H, exchangeable with D2O, NHCH3), 7.10 (pseudo t, J=7.9 and 7.6 Hz, 1 H, H-16), 7.38 (d, J=7.6 Hz, 1 H, H-17), 7.57 (d, J=7.6 Hz, 1 H, H-15), 7.67 (s, 1 H, H-13), 7.35 (s, 1 H, H-8), 7.83 (br s, 1 H, exchangeable with D2O, NH).

Workup

  1. customAfter removal of volatiles in vacuo
  2. customthe residue was triturated with methanol-water
  3. customthe solid that formed
  4. filtrationwas collected by suction filtration
  5. washwashed with water (10 mL)
  6. customdried

Sources & evidence

ORD record
ord-46f250d9b8484b1980fc7aa1cd851d3b
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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