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Sodium ethoxide → HCID 11283254, compound

HRID 458408
Notes
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Reaction equation

HRID 458408 reaction equation
[CH2:1]([O:3][C:4]([C:6]([C:17](=O)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[CH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)=[O:5])[CH3:2].CC[O-].[Na+].Cl.[NH2:33][C:34]1[N:38]2[CH2:39][CH2:40][CH2:41][N:37]2[C:36](=[O:42])[CH:35]=1>CCO>[CH2:1]([O:3][C:4]([C:6]1[CH:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[C:35]2[C:36](=[O:42])[N:37]3[CH2:41][CH2:40][CH2:39][N:38]3[C:34]=2[NH:33][C:17]=1[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 674357711H,5H-Pyrazolo[1,2-a]pyrazol-1-one, 3-amino-6,7-dihydro-, hydrochloride (1:1)HCID 69516430HCID 69516430, compound

Product 1

HCID 11283254HCID 11283254, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Step C (920 mg, 2.48 mmol) and NaOEt (170 mg, 2.50 mmol) were added portionwise to a stirred solution of 3-amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one hydrochloride (refs. R. B. Greenwald, U.S. Pat. No. 4,128,425 and E. E. Boros, F. Bouvier, S. Randhawa and M. H. Rabinowitz, J. Heterocyclic Chem., 2001, 38, 613–616.) (440 mg, 2.51 mmol) in EtOH (6 mL). The reaction mixture was heated at reflux for 5.5 h and then allowed to cool to rt and filtered to remove NaCl. The filtrate was concentrated at reduced pressure and the remaining material was triturated with CH2Cl2 to yield D as an off-white solid (500 mg, 1.02 mmol, 41%): 1H NMR (400 MHz, DMSO-d6) δ 12.63 (br, 1H), 9.76 (s, 1H), 7.77 (d, 2H, J=8), 7.27 (dd, 2H, J=8, 6), 7.20 (d, 2H, J=8), 7.11 (t, 2H, J˜9), 4.76 (s, 1H), 3.87 (q, 2H, J=7), 3.42 (m, 2H), 3.27 (m, 2H), 2.98 (m, 2H), 2.85 (m, 2H), 2.26 (m, 2H), 0.96 (t, 3H, J=7) ppm; ESI-MS m/z 492 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5.5 h
  3. filtrationfiltered
  4. customto remove NaCl
  5. concentrationThe filtrate was concentrated at reduced pressure
  6. customthe remaining material was triturated with CH2Cl2

Sources & evidence

ORD record
ord-e2c7beb1f9c44a908eaffc38b4a9fddb
Source dataset
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07189851B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes