Formamidine acetate → HCID 9885714, compound

HRID 1790017Notes

Reaction equation

HRID 1790017 reaction equation
N[C:2]1[C:6]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:5][N:4]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)[C:3]=1[C:25]#[N:26].C(O)(=O)C.[CH:31]([NH2:33])=[NH:32]>C(O)C>[CH:7]1([C:6]2[C:2]3[N:32]=[CH:31][N:33]=[C:25]([NH2:26])[C:3]=3[N:4]([C:12]3[CH:13]=[CH:14][C:15]([O:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:16][CH:17]=3)[CH:5]=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 22037807HCID 22037807, compound

Product 1

HCID 9885714HCID 9885714, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of the 3-amino-4-cyclopentyl-1-(4-phenoxyphenyl)-1H-2-pyrrolecarbonitrile (185 mg, 0.539 mmol) in absolute ethanol (10 mL) was treated with formamidine acetate (450 mg, 4.33 mmol) then heated at 85° C. for 2 hours. The solvent was evaporated under reduced pressure then the residue was purified by preparative reverse phase HPLC to provide 145 mg (73%) of the title compound as a white solid after lyophilization: 1H NMR (DMSO-d6, 400 MHz) δ 8.19 (s, 1H), 7.44 (m, 5H), 7.19 (t, 1H), 7.13 (m, 4H), 5.79 (bs, 2H), 3.23 (m, 1H), 2.05 (m, 2H), 1.77 (m, 4H), 1.64 (m, 2H); RP-HPLC (Hypersil HS-C18, 5 μm, 100 A, 4.6×250 mm; 5%–100% acetonitrile-0.05 M ammonium acetate over 25 min, 1 mL/min) tr 23.3 min.; MS: MH+ 371.5.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-7a119e6b380e48b1928402a388d28815
Source dataset
uspto-grants-2006_07
Patent number
US07071199B1

Reaction notes

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