P,P-Diphenylphosphinic azide → 1-(4-Dimethylaminomethyl-2-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-urea

HRID 1821801Notes

Reaction equation

HRID 1821801 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[NH2:10])=[N:6][CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:29][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36](N)=[C:35]([O:40][CH3:41])[CH:34]=1)[CH3:31]>>[CH3:31][N:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([NH:10][C:9]([NH:8][C:5]2[CH:4]=[N:3][C:2]([CH3:1])=[CH:7][N:6]=2)=[O:11])=[C:35]([O:40][CH3:41])[CH:34]=1)[CH3:29]

Participants

4

Reactant 3

HCID 199401P,P-Diphenylphosphinic azideHCID 22046266(5-Methyl-pyrazin-2-yl)-urea2×HCID 220462864-((Dimethylamino)methyl)-2-methoxyaniline

Product 1

HCID 220464981-(4-Dimethylaminomethyl-2-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-urea

Procedure

144-Dimethylaminomethyl-2-methoxy-phenyl)-3-(5methyl-pyrazin-2-yl)urea. According to the diphenylphosphoryl azide method described above for compound 336, 4-dimethylaminomethyl-2-methoxy-phenylamine was converted to the (5-methyl-pyrazin-2-yl)-urea. The crude product was purified by preparative TLC, eluting with 5% MeOH in CH2Cl2. 1H NMR (400 MHz, d6-DMSO): δ 11.21 (s, 1H), 8.95 (s, 1H), 8.39 (s, 1H), 8.21 (d, J=7.83 Hz, 1H), 8.04 (s, 1H), 7.01 (s, 1H), 6.89 (d, J=7.83 Hz, 1H), 3.98 (s, 3H), 3.92 (s, 2H), 2.26 (s, 3H), 2.24 (s, 6H). MS APCI-Pos, M+1=316.0.

Workup

  1. customThe crude product was purified by preparative TLC
  2. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-130b24b259f44314a5a1eb9b06d7cc25
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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