Hydrochloric Acid → 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid

HRID 1515013Notes

Reaction equation

HRID 1515013 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:16][C:15]3[CH:17]=[C:18]([C:21](=[O:33])[NH:22][C:23]4[CH:32]=[CH:31][C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[N:24]=4)[CH:19]=[CH:20][C:14]=3[N:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[NH:22][C:21]([C:18]1[CH:19]=[CH:20][C:14]2[N:13]=[C:12]([C:9]3[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[CH:7][CH:8]=3)[NH:16][C:15]=2[CH:17]=1)=[O:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 669657603-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester

Product 1

HCID 669652573-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid methyl ester was taken up in MeOH (5 mL) then 1N NaOH (5 mL) was added. The solution was stirred at ambient temperature for 3 h then the solution was carefully acidified to pH 3-4 with 1N HCl. The suspension was filtered, washed with water, and dried under reduced pressure to give 3-{4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid. 1H NMR (MeOD, 400 MHz): δ 8.45-8.43 (d, J=8.97 Hz, 1H), 8.38-8.36 (d, J=8.97 Hz, 2H), 8.04-8.01 (dd, J=1.77 Hz, 8.59 Hz, 1H), 7.92-7.90 (d, J=8.34 Hz, 2H), 7.77-7.71 (m, 2H), 7.54-7.51 (t, J=7.83 Hz, 1H), 7.1 (s, 2H), 2.96-2.92 (t, J=7.45 Hz, 2H), 2.65-2.62 (t, J=7.71 Hz, 2H), 2.16 (s, 6H). MS (ESI) m/z 465.1 (M+H).

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-06086439cdc445818cba796176d9843f
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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