Dimethylformamide → HCID 23440764, compound

HRID 1358008Notes

Reaction equation

HRID 1358008 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.O[N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2N=N1.Cl.CN(C)[CH2:25][CH2:26][CH2:27]N=C=NCC.[CH3:34]N(C)C=O>>[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([NH:13][C:17]2[C:16]3[C:21](=[CH:34][CH:27]=[CH:26][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 121223'-Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 23440764HCID 23440764, compoundYield 94%

Procedure

To a solution of 3-hydroxyphenylacetic acid (3.04 g, 20 mmol) in dimethylformamide (30 mL) and 1-hydroxybenzotriazole (3.24 g, 24 mmol) at 0° C. under nitrogen was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.60 g, 24 mmol). After 30 minutes, 1-aminonaphthyline (2.86 g, 20 mmol) was added, and the mixture was stirred overnight at room temperature. The reaction was quenched with 5% hydrochloride and extracted with ethyl acetate. The organic layer was washed with a 10% sodium carbonate solution, washed with brine, dried over MgSO4, filtered, and concentrated to provide the title compound (5.239 g, 94% yield): 1H NMR (DMSO-d6) 9.66 (br, 1H), 9.04 (s, 1H), 7.96 (dd, 1H), 7.85 (dd, 1H), 7.74 (dd, 1H), 7.68 (d, 1H), 7.18-7.49 (m, 3H), 7.16 (t, 1H), 6.92 (m 2H), 6.73 (d, 1H), 3.76 (s, 2H); ES-MS (m/z) 278 [M+H]+.

Workup

  1. addition1-aminonaphthyline (2.86 g, 20 mmol) was added
  2. customThe reaction was quenched with 5% hydrochloride
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a 10% sodium carbonate solution
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4b51a72649044565845297ebd4ef466e
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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