Formic Acid → HCID 178507110, compound

HRID 80701

Reaction equation

HRID 80701 reaction equation
C(OC(=O)[NH:10][C:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][N:13]1[C:20](=[O:46])[C:21]([O:38]CC3C=CC=CC=3)=[C:22]([C:24]3[NH:25][C:26]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)=[C:27](Cl)[N:28]=3)[N:23]=[C:12]21)C1C=CC=CC=1.C(O)=O>CO.[Pd]>[NH2:10][C:11]12[CH2:17][CH2:16][CH:15]([CH2:18][CH2:19]1)[CH2:14][N:13]1[C:20](=[O:46])[C:21]([OH:38])=[C:22]([C:24]3[NH:28][CH:27]=[C:26]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[N:25]=3)[N:23]=[C:12]21

Participants

5

Reactant 2

HCID 284Formic AcidHCID 117616853benzyl(3-(benzyloxy)-2-(4-chloro-5-(4-fluorobenzyl)-1H-imidazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate

Product 1

HCID 178507110HCID 178507110, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of benzyl(3-(benzyloxy)-2-(4-chloro-5-(4-fluorobenzyl)-1H-imidazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate, Intermediate 6 (60 mg, 0.092 mmol) in MeOH (3 mL) was added formic acid (0.100 mL, 2.65 mmol) followed by 10% Pd/C (98 mg, 0.092 mmol) and the mixture stirred at 40° C. for 3 h. After cooling to room temperature, the mixture was filtered through a pad of celite and concentrated. The mixture was then treated with sat. NaHCO3, extracted with dichloromethnae (×4), dried (Na2SO4), filtered and concentrated to afford the title compound (30 mg, 83% yield) as a light purple solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 1.53-1.60 (m, 2H), 1.73-1.81 (m, 6H), 2.37 (br. s., 1H), 2.51-2.54 (m, 2H), 3.93-3.99 (m, 2H), 4.01 (d, J=3.66 Hz, 2H), 7.10-7.17 (m, 3H), 7.30 (dd, J=8.24, 5.80 Hz, 2H). LCMS (M+H)=396.13.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through a pad of celite
  3. concentrationconcentrated
  4. additionThe mixture was then treated with sat. NaHCO3
  5. extractionextracted with dichloromethnae (×4)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4dae1b8a5d654082b51557eb41856b84
Source dataset
uspto-grants-2014_09
Patent number
US08846659B2

Linked notes

Loading…