Hydrogen Bromide → HCID 17985223, compound

HRID 1432927Notes

Reaction equation

HRID 1432927 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH:12]1[CH2:18][O:19][CH3:20])=O)C1C=CC=CC=1.I[C:22]1[C:23]([NH2:28])=[N:24][CH:25]=[CH:26][CH:27]=1.Br>C(O)(=O)C>[NH2:28][C:23]1[C:22]2[C:23](=[CH:22][C:27]([CH2:26][N:14]3[CH2:15][CH2:16][NH:11][CH:12]([CH2:18][O:19][CH3:20])[C:13]3=[O:17])=[CH:26][CH:27]=2)[N:24]=[CH:25][N:24]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 27631512-Amino-3-iodopyridineHCID 54412263HCID 54412263, compound

Product 1

HCID 17985223HCID 17985223, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2-methoxymethyl-3-oxo-piperazine-1-carboxylic acid benzyl ester (5.8 g, 13.3 mmol) in 50 mL of acetic acid is added dropwise, 20 mL of a 30%HBr in AcOH solution. The solution is stirred for 1 hour. After this time, the solution is concentrated. The resulting crude product is purified by column chromatography eluting with CH2Cl2:MeOH:NH4OH (20:5:1). The title compound (2.0 g, 6.6 mmol) is obtained as a white solid. 1H NMR (d6-DMSO, 300 MHz) δ8.60 (s, 1H), 7.72 (m, 2H), 7.48 (d, 1H), 5.60 (bs, 2H), 4.72 (AB, 2H), 3.87 (m, 2H), 3.71 (m, 1H), 3.42 (m, 1H), 3.40 (s, 3H), 3.19 (m, 2H), 3.02 (m, 1H). MS (ion spray) m/z 302, (M+H).

Workup

  1. concentrationAfter this time, the solution is concentrated
  2. customThe resulting crude product is purified by column chromatography
  3. washeluting with CH2Cl2:MeOH:NH4OH (20:5:1)

Sources & evidence

ORD record
ord-7c87a04d46d2483886772d51328d22a5
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

Loading…