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Formamidine acetate → HCID 57758181, compound

HRID 2197524
Notes
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Reaction equation

HRID 2197524 reaction equation
C(O)(=O)C.[CH:5](N)=[NH:6].[NH2:8][N:9]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=2)[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10]1>C(O)CCC>[NH2:15][C:14]1[C:13]2=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:23])[CH:17]=3)[C:11]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:10][N:9]2[N:8]=[CH:5][N:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 66786981ethyl 1-amino-4-(4-amino-3-fluorophenyl)-5-cyano-1H-pyrrole-3-carboxylate

Product 1

HCID 57758181HCID 57758181, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Formamidine acetate (22.4 g, 215 mmol) was added to a suspension of ethyl 1-amino-4-(4-amino-3-fluorophenyl)-5-cyano-1H-pyrrole-3-carboxylate (6.2 g, 21.5 mmol) in n-butanol (100 mL). The reaction was heated (100° C.) for 16 h and then cooled to rt. The solvent was removed under reduced pressure and then ethanol (50 mL) and water (200 mL) were added. The mixture was stirred for 30 min and the resulting precipitate was collected by filtration. The solid was washed with water (2×50 mL) and dried to afford desired product (5.80 g, 85%); 1H NMR (300 MHz, DMSO-d6) δ 8.08 (s, 1H), 8.00-8.10 (br s, 1H), 7.90 (s, 1H), 7.03 (dd, J=12.3, 1.9 Hz, 1H), 6.77-6.88 (m, 2H), 5.36 (s, 2H), 5.21-5.31 (br s, 1H), 4.06 (q, J=7.1 Hz, 2H), 1.11 (t, J=7.1 Hz, 3H); ES-MS m/z 316.4 (MH)+; HPLC RT (Method B) 2.39 min.

Workup

  1. temperaturecooled to rt
  2. customThe solvent was removed under reduced pressure
  3. additionethanol (50 mL) and water (200 mL) were added
  4. filtrationthe resulting precipitate was collected by filtration
  5. washThe solid was washed with water (2×50 mL)
  6. customdried

Sources & evidence

ORD record
ord-5f6fb708a09b4f8888c184a1931bb29e
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08338594B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes