Dimethylformamide → HCID 69048230, compound

HRID 925077Notes

Reaction equation

HRID 925077 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=O.CC[N:16]([CH:20]([CH3:22])[CH3:21])C(C)C.C[N:24](C)[CH:25]=[O:26]>CO>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([NH:16][C:20]1[CH:22]=[CH:8][CH:2]=[C:3]([CH2:4][CH2:22][C:20]2[C:21]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:25](=[O:26])[NH:24][N:16]=2)[CH:21]=1)=[O:7]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 728713-Benzoylpropionic acidHCID 81531Diisopropylethylamine

Product 1

HCID 69048230HCID 69048230, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-oxo-4-phenylbutanoic acid (50 mg, 0.28 mmol), 2-(3H-(1,2,3)triazolo(4,5-b)pyridin-3-yl)-1,1,3,3-tetramethylisouroniumhexafluorophosphate (V) (106 mg, 0.28 mmol) and Hunig's base (120 mg, 0.9 mmol) in anhydrous N,N-dimethylformamide (0.5 ml) was stirred at room temperature for 10 minutes, and EXAMPLE 260 (50 mg, 0.18 mmol) was added in one portion. The reaction mixture was stirred at room temperature for another 1 hour, and was diluted with 5 mL of methanol. The solid material was collected by filtration, washed with methanol, and dried to provide the title compound. MS (DCI/NH3) m/z 430 (M+H)+. 1H NMR (300 MHz, dimethylsulfoxide-d6): δ 1.54-1.77 (m, 4H), 2.30-2.42 (m, 2H), 2.42-2.49 (m, 2H), 2.65-2.79 (m, 4H), 2.79-2.89 (m, 2H), 3.30-3.38 (m, 2H), 6.90 (d, J=7.80 Hz, 1H), 7.19 (t, J=7.80 Hz, 1H), 7.38-7.49 (m, 2H), 7.54 (t, J=7.46 Hz, 2H), 7.61-7.69 (m, 1H), 7.99 (t, J=6.61 Hz, 2H), 9.96 (s, 1H), 12.52 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 1 hour
  2. filtrationThe solid material was collected by filtration
  3. washwashed with methanol
  4. customdried

Sources & evidence

ORD record
ord-e74f1484d9e24d7284f42c72b42adbc4
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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