4-Fluorobenzoyl chloride → HCID 58859688, compound

HRID 1349572Notes

Reaction equation

HRID 1349572 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:23](=[O:32])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@@H:15]([CH3:33])[CH2:14]2)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].FC1C=CC(C(Cl)=O)=CC=1.[BH4-].[Na+]>C(O)C.[Co](Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:23](=[O:32])[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@@H:15]([CH3:33])[CH2:14]2)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([N:9]([C@H:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:23](=[O:32])[C:24]3[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=3)[C@@H:15]([CH3:33])[CH2:14]2)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 4311764Sodium borohydrideHCID 68921706HCID 68921706, compound2×

Product 2

HCID 58859688HCID 58859688, compoundYield 10%HCID 68921706HCID 68921706, compound

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 702EthanolSolvent

Procedure

(2S,4R)-N-(3-Aminomethyl-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared from (2S, 4R)-N-(3-cyano-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. (2S,4R)-N-(3-cyano-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared following standard procedure C, substituting 3-cyanophenylboronic acid for 4-fluorobenzoyl chloride. To a mixture of (2S, 4R)-N-(3-cyano-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (48 mg, 0.1 mmol) in 2 ml ethanol was added cobalt chloride (14 mg, 0.11 mmol). Sodium borohydride (12 mg, 0.33 mmol) was added at 0° C., and the temperature was held at 0° for 30 min. The mixture was then warmed to rt, and stirred overnight. The reaction was quenched by adding saturated aqueous ammonium chloride. The separated aqueous layer was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude oil was purified by HPLC to give the title compound (10 mg, 10%).

Workup

  1. customThe reaction was quenched
  2. additionby adding saturated aqueous ammonium chloride
  3. extractionThe separated aqueous layer was extracted with ethyl acetate
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude oil was purified by HPLC

Sources & evidence

ORD record
ord-ad573361c1ec448182f5bd7b586eea7f
Source dataset
uspto-grants-2007_05
Patent number
US07211672B2

Reaction notes

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