Hydrochloric Acid → HCID 16722502, compound

HRID 555277Notes

Reaction equation

HRID 555277 reaction equation
[CH3:1][S:2]([CH2:5][O:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:12]=2[N:11]=[CH:10]1)(=[O:4])=[O:3].[NH:21]1[CH:30]2[CH:25]([CH2:26][CH2:27][CH2:28][CH2:29]2)[CH2:24][CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.Cl>CN(C=O)C>[CH3:1][S:2]([CH2:5][O:6][CH2:7][CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([N:21]3[CH:30]4[CH:25]([CH2:26][CH2:27][CH2:28][CH2:29]4)[CH2:24][CH2:23][CH2:22]3)=[O:20])=[CH:17][C:12]=2[N:11]=[CH:10]1)(=[O:3])=[O:4]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 92911DecahydroquinolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66987155HCID 66987155, compound

Product 1

HCID 16722502HCID 16722502, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2-methanesulfonylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid (0.5 g, 1.677 mmol) in DMF (5 mL) was added decahydroquinoline (0.257 g, 1.845 mmol) followed by HOBt (0.25 g, 1.845 mmol) and DIPEA (0.65 g, 5 mmol). The reaction mixture was cooled to 0° C. and EDCl.HCl (0.354 g, 1.845 mmol) was added. It was gradually raised to ambient temperature and stirring continued for 12 h. The solvent was then evaporated, the residue diluted with water (5 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic phases were washed with brine solution, dried (Na2SO4) and the solvent evaporated affording the crude amide which was purified by preparative HPLC to give 0.3 g (43%) of [1-(2-methanesulfonylmethoxy-ethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone. MS-ESI m/z 420 (M+1): 1H NMR (300 MHz, DMSO-d6) δ 1.1-1.9 (br, 13H), 2.8 (s, 3H), 3.0-3.3 (m, 2H), 4.15 (t, 2H), 4.5 (t, 2H), 4.65 (s, 2H), 7.3 (m, 1H), 7.6 (m, 1H), 7.7 (d, 1H), 8.3 (s, 1H)

Workup

  1. temperatureIt was gradually raised to ambient temperature
  2. customThe solvent was then evaporated
  3. additionthe residue diluted with water (5 mL)
  4. extractionextracted with CH2Cl2 (3×25 mL)
  5. washThe combined organic phases were washed with brine solution
  6. dry with materialdried (Na2SO4)
  7. customthe solvent evaporated
  8. customaffording the crude amide which
  9. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-c3ba721787fb48729b58110ed90a41a9
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

Loading…