Triethylamine → HCID 67070834, compound

HRID 732039Notes

Reaction equation

HRID 732039 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O.[Cl:12][CH2:13][C:14]([NH:16]O)=[NH:15].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[Cl:12][CH2:13][C:14]1[N:16]=[C:6]([C:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:11]=[CH:10][CH:9]=2)[O:8][N:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 185629Benzoic acid, 3-(hydroxymethyl)-HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178511097HCID 178511097, compound

Product 1

HCID 67070834HCID 67070834, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Hydroxymethylbenzoic acid, described in Reed, G. A.; Dimmel, D. R.; Malcolm, E. W. J. Org. Chem. 1993, 58 (23), 6372-6376, (175 mg, 1.15 mmol), 2-chloro-N-hydroxy-acetamidine (125 mg, 1.15 mmol) and HBTU was dissolved in anhydrous DMF (4 ml). Triethylamine (0.48 ml, 3.5 mmol) was added and the reaction was stirred at ambient temperature over night. The crude product was partitioned between dichloromethane and NaHCO3 (aq), the organic phase was dried (MgSO4) and the dichloromethane was removed in vacuo. The resulting DMF-solution was heated at 120° C. over night. The reaction mixture was concentrated in vacuo and the title compound (64 mg, 25%) was isolated by flash chromatography using 25-50% ethyl acetate in heptane. 1H NMR (CDCl3), δ (ppm): 8.15 (s, 1H), 8.06 (d, 1H), 7.62 (d, 1H), 7.53 (t, 1H); 4.80 (d, 2H), 4.66 (s, 1H); 1.99 (br. t, 1H).

Workup

  1. customThe crude product was partitioned between dichloromethane and NaHCO3 (aq)
  2. dry with materialthe organic phase was dried (MgSO4)
  3. customthe dichloromethane was removed in vacuo
  4. temperatureThe resulting DMF-solution was heated at 120° C. over night
  5. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-033d605065f34e83b2dcea8a47dcb8d3
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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