Acetic Acid → 10-Amino-2-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-3-hydroxy-7,8,9,10-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-4(6H)-one

HRID 80695Notes

Reaction equation

HRID 80695 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:45])[C:21]([O:37]CC3C=CC=CC=3)=[C:22]([C:24]3[O:25][C:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[N:27][N:28]=3)[N:23]=[C:12]21)C1C=CC=CC=1.Br.C(O)(=O)C>C(Cl)Cl>[NH2:10][C:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][N:13]1[C:20](=[O:45])[C:21]([OH:37])=[C:22]([C:24]3[O:25][C:26]([CH2:29][C:30]4[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=4)=[N:27][N:28]=3)[N:23]=[C:12]21

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 71100906benzyl(3-(benzyloxy)-2-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate

Product 1

HCID 13641318610-Amino-2-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-3-hydroxy-7,8,9,10-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-4(6H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl(3-(benzyloxy)-2-(5-(4-fluorobenzyl)-1,3,4-oxadiazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate, Intermediate 11 (30 mg, 0.048 mmol) in CH2Cl2 (2 mL) was added HBr in acetic acid (0.218 mL, 1.206 mmol) and the mixture stirred at room temperature for 16 h. The mixture was concentrated and dried under high vacuum to afford the title compound (18 mg, 0.038 mmol, 78% yield) as a brown solid. 1H NMR (500 MHz, MeOD) δ ppm 7.39-7.46 (2H, m), 7.08-7.14 (2H, m), 4.38 (2H, s), 4.20 (2H, d, J=3.66 Hz), 2.60 (1H, br. s.), 2.22-2.31 (2H, m), 2.05-2.18 (4H, m), 1.85-1.94 (2H, m). LCMS (M+H)=398.18.

Workup

  1. concentrationThe mixture was concentrated
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-c374301542724c509731ce514eccc92a
Source dataset
uspto-grants-2014_09
Patent number
US08846659B2

Reaction notes

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