Acetic Acid → HCID 53892810, compound

HRID 1433021Notes

Reaction equation

HRID 1433021 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:10][N:9]([C:11](=[O:20])[CH2:12][O:13][C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:8][C:7](=[O:21])[N:6]1[CH2:22][C:23]1[CH:28]=C[C:26](C#N)=[C:25](N)[CH:24]=1)=[O:4].[N:32]1[CH:37]=[N:36][CH:35]=[N:34][CH:33]=1.CC(O)=O>CCO>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][N:9]([C:11](=[O:20])[CH2:12][O:13][C:14]2[S:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[CH2:8][C:7](=[O:21])[N:6]1[CH2:22][C:23]1[CH:28]=[C:33]2[C:26]([C:37]([NH2:32])=[N:36][CH:35]=[N:34]2)=[CH:25][CH:24]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 92621,3,5-TriazineHCID 53970653HCID 53970653, compound

Product 1

HCID 53892810HCID 53892810, compoundYield 40.8%

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 methyl ester (110 mg, 0.25 mmol), 1,3,5-triazine (207 mg, 2.55 mmol), and glacial HOAc (157 mg, 2.55 mmol) in absolute EtOH (5 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 50 mg (32%) of the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) δ3.34-3.89 (m, 2H), 3.60 (s, 3H), 4.14-4.54 (m, 3H), 4.64 (br d, J=14.4 Hz, 1H), 4.78-5.11 (m, 3H), 6.19 (d, J=4.1 Hz, 1H), 6.73 (d, J=4.1 Hz, 1H), 7.64 (s, 1H), 7.65 (d, J=9.0 Hz, 1H), 8.34 (d, J=9.0 Hz, 1H), 8.79 (s, 1H), 9.71 (br s, 2H) ppm; MS (ion spray): m/z 490 (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-1455b21cabfc40b4983ca35c3d76d09a
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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