Acetic Acid → HCID 53638350, compound

HRID 1433023Notes

Reaction equation

HRID 1433023 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]#[N:30])[CH2:5][N:6]1[C:11](=[O:12])[CH2:10][N:9]([C:13](=[O:22])[CH2:14][O:15][C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[CH2:8][CH:7]1[C:23]([OH:25])=[O:24].[N:31]1C=NC=N[CH:32]=1.CC(O)=O>CCO>[NH2:30][C:29]1[C:28]2[C:2](=[CH:3][C:4]([CH2:5][N:6]3[C:11](=[O:12])[CH2:10][N:9]([C:13](=[O:22])[CH2:14][O:15][C:16]4[S:17][C:18]([Cl:21])=[CH:19][CH:20]=4)[CH2:8][CH:7]3[C:23]([OH:25])=[O:24])=[CH:26][CH:27]=2)[N:1]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 92621,3,5-TriazineHCID 54262192HCID 54262192, compound

Product 1

HCID 53638350HCID 53638350, compoundYield 105.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing (+/−)-1-(3-amino-4-cyano-benzyl)-4-[(5-chloro-thiophen-2-yloxy)-acetyl]-6-oxo-piperazine-2-carboxylic acid (20 mg, 0.03 mmol), 1,3,5-triazine (28 mg, 0.34 mmol), and glacial HOAc (20 mg, 0.34 mmol) in absolute EtOH (6 mL) is maintained at reflux for 16 hours. The reaction mixture is concentrated to dryness and then purified by reverse-phase HPLC [Buffer A: water w/0.1% TFA; Buffer B: CH3CN w/0.1% TFA; Gradient: 0% B to 60% B over 30 min] to provide 15 mg (75%) of the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) δ3.75-4.38 (m, 5H), 4.67 (d, J=14.8 Hz, 1H), 4.79 (d, J=15.3 Hz, 1H), 4.95 (m, 1H), 5.09 (br d, J=16.0 Hz, 1H), 6.18 (m, 1H), 6.71 (m, 1H), 7.64 (m, 2H), 8.31 (d, J=8.5 Hz, 1H), 8.75 (s, 1H), 9.64 (br s, 2H) ppm; MS (ISP loop): m/z 476 (M+H).

Workup

  1. temperatureis maintained
  2. temperatureat reflux for 16 hours
  3. concentrationThe reaction mixture is concentrated to dryness
  4. custompurified by reverse-phase HPLC [Buffer A: water

Sources & evidence

ORD record
ord-1b9f067ec81446b88445157a37ebc9ea
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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