Water → HCID 66965859, compound

HRID 1515028Notes

Reaction equation

HRID 1515028 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH:16]=O)=[C:11]([Cl:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:20][C:21]1[CH:22]=[C:23]([CH:37]=[CH:38][C:39]=1[NH2:40])[C:24]([NH:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=1)=[O:25].OOS([O-])=O.[K+].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:19])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([C:16]2[NH:20][C:21]3[CH:22]=[C:23]([C:24](=[O:25])[NH:26][C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[CH:37]=[CH:38][C:39]=3[N:40]=2)=[C:11]([Cl:18])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 669657403,4-diamino-N-quinolin-2-yl-benzamideHCID 866328253-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

Product 1

HCID 66965859HCID 66965859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(3,5-dichloro-4-formylphenyl)-propionic acid tert butyl ester (440 mg, 0.8 mmol), 3,4-diamino-N-quinolin-2-yl-benzamide (403 mg, 1 eq) and oxone (600 mg, 0.67 eq) in DMF (10 mL)/H2O (1 mL) was stirred vigorously open to air for 1 h. The mixture was partitioned between water and ethyl acetate. The ethyl acetate fractions were dried over magnesium sulphate and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography to give 3-{3,5-dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-propionic acid tert-butyl ester as an orange foam. 1H-NMR (CDCl3, 400 MHz): δ 8.60 (d, J=8.97 Hz, 1H), 8.38 (s, 1H), 8.21-8.29 (m, 1H), 7.95 (dd, J=8.34, 1.26 Hz, 1H), 7.82-7.91 (m, 2H), 7.71 (ddd, J=8.37, 6.98, 1.33 Hz, 2H), 7.47-7.56 (m, 1H), 7.17-7.24 (m, 2H), 2.85 (t, J=7.33 Hz, 2H), 2.50-2.57 (m, 2H), 1.42-1.48 (m, 10H).

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. dry with materialThe ethyl acetate fractions were dried over magnesium sulphate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3686cf15beea4051ad470f94b888942f
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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