Carbonic acid-guanidine (1:1) → HCID 25002413, compound

HRID 1015342Notes

Reaction equation

HRID 1015342 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][CH:21]=[C:20](F)[C:17]=3[C:18]#[N:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.C(=O)(O)O.[NH2:31][C:32]([NH2:34])=[NH:33]>CC(N(C)C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]3[CH:23]=[CH:22][CH:21]=[C:20]4[C:17]=3[C:18]([NH2:19])=[N:33][C:32]([NH2:34])=[N:31]4)[CH2:12][CH2:13]2)=[O:7])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 286947Carbonic acid-guanidine (1:1)HCID 66924408HCID 66924408, compound

Product 1

HCID 25002413HCID 25002413, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2-[1-(4-Chlorobenzoyl)piperidin-4-ylmethoxy]-6-fluorobenzonitrile (110 mg, 0.3 mmol) and guanidine carbonate (53 mg; 0.3 mmol) were heated at 140° C. in dimethylacetamide for 4 hours. The mixture was cooled and triturated with water for 45 minutes. Solids were filter off and triturated with 3 mL of ethanol. Solids were collected by filtration and dried to afford 75 mg of title compound (59% yield) 1HNMR (400 MHz, DMSO-d6) δ 7.52 (m, 2H), 7.43 (m, 2H), 7.35 (t, J=8.4 Hz, 1H), 7.17 (br d, J=15.2 Hz, 2H), 6.77 (dd, J=8.4, 0.8 Hz, 1H), 6.54 (d, J=7.2 Hz, 1H), 5.95 (br s, 2H), 4.51 (br s, 1H), 4.03 (d, J=6.4 Hz, 2H), 3.59 (br s, 1H), 3.11 (br s, 1H), 2.84 (br s, 1H), 2.22 (m, 1H), 1.87 (br s, 1H), 1.76 (br s, 1H), 1.3 (br d, J=10.4 Hz, 2H). MS m/z (ESI) 412 (M−H)+.

Workup

  1. temperatureThe mixture was cooled
  2. customtriturated with water for 45 minutes
  3. filtrationSolids were filter off
  4. customtriturated with 3 mL of ethanol
  5. filtrationSolids were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-b1445532626344c098a53d50ee74310c
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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