Veratrylamine → HCID 25230949, compound

HRID 2272939Notes

Reaction equation

HRID 2272939 reaction equation
Cl[C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1.COC1C=C(C=CC=1OC)C[NH2:32]>CC(N(C)C)=O.FC(F)(F)C(O)=O.C(OC(=O)C)C>[NH2:32][C:2]1[S:10][C:9]2[C:8]([C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[O:12])=[N:7][C:6]([NH:18][CH2:19][C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)=[N:5][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 79832VeratrylamineHCID 46883208HCID 46883208, compound

Product 1

HCID 25230949HCID 25230949, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
170 °C

Procedure

A stirred solution of Example 5 (0.055 g, 0.143 mmol) in dimethylacetamide (2 ml) was treated with 3,4-dimethoxybenzylamine (0.22 ml, 1.43 mmol). The solution was heated to 170° C. for 30 min in a microwave reactor. The cooled solution was reduced in vacuo and taken up in neat trifluoroacetic acid (3 ml). The mixture was stirred at 70° C. for 48 h, cooled and reduced in vacuo. The residue was taken up in ethylacetate (25 ml), washed with saturated sodium bicarbonate solution (15 ml), dried over sodium sulfate and reduced in vacuo. Silica gel (10 g) column chromatography (10% MeOH in EtOAc) afforded the title compound as an orange solid in 9% yield, >95% purity. LC-MS m/z=368.0 [M+H]+; RT=2.58; LC-MS method 1. 1H NMR: δH (400 MHz, D6-DMSO) 4.67 (2H, bd), 5.81 (1H, s), 7.23-7.25 (1H, m), 7.33-7.36 (1H, m), 7.51 (2H, b), 7.79 (1H, bd), 8.09 (1H, bd), 8.38-8.62 (4H, bm)

Workup

  1. temperaturecooled
  2. washwashed with saturated sodium bicarbonate solution (15 ml)
  3. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-4021adcb5553492391ed59a3160e7180
Source dataset
uspto-grants-2015_09
Patent number
US09120807B2

Reaction notes

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