Dimethylformamide → HCID 178491083, compound

HRID 2236773Notes

Reaction equation

HRID 2236773 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([OH:9])[C:6]([O:10][CH3:11])=[CH:5]N=1.CO[CH:14]=[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[CH:26]3)[CH:23]=2)[C:18](=[O:30])[NH:17][C:16]1=[O:31].[CH3:32]N(C)C=O>>[OH:9][C:7]1[CH:8]=[C:3]([CH:32]=[CH:5][C:6]=1[O:10][CH3:11])[CH2:2][NH:1][CH:14]=[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([N:25]3[CH:29]=[CH:28][CH:27]=[CH:26]3)[CH:23]=2)[C:18](=[O:30])[NH:17][C:16]1=[O:31]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 686931254-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dioneHCID 178493746HCID 178493746, compound

Product 1

HCID 178491083HCID 178491083, compound

Procedure

A mixture of 2-aminomethyl-5-methoxy-pyridin-4-ol (123 mg, 0.80 mmole), 4 mL of N,N-dimethylformamide and 4-methoxymethylene-6-pyrrol-1-yl-4H-isoquinoline-1,3-dione (215 mg, 0.80 mmole) is added and the reaction mixture stirred for one hour. The reaction mixture is evaporated to dryness and treated with acetonitrile, the solid filtered and dried to give a white solid, 199 mg, (65%), mp 199-209° C. dec; MS (ES+): m/z 391.1 (M+H).

Workup

  1. additionis added
  2. customThe reaction mixture is evaporated to dryness
  3. additiontreated with acetonitrile
  4. filtrationthe solid filtered
  5. customdried
  6. customto give a white solid, 199 mg, (65%), mp 199-209° C. dec

Sources & evidence

ORD record
ord-14c86a5bcdc148d0956699dd20584f76
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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