HCID 11216309, compound → HCID 10394361, compound

HRID 1986646Notes

Reaction equation

HRID 1986646 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N:35](C(C2C=NC(Cl)=CC=2)=O)[S:36]([CH3:39])(=[O:38])=[O:37])[C:8]([O:33][CH3:34])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28](Cl)=[N:27][CH:26]=4)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>COC[C@@H](N)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])[C:8]([O:33][CH3:34])=[C:9]([NH:11][C:12]([C:14]2[S:18][C:17]3[C:19]([NH:23][C:24](=[O:32])[C:25]4[CH:30]=[CH:29][C:28]([NH:35][C@@H:7]([CH3:6])[CH2:8][O:33][CH3:34])=[N:27][CH:26]=4)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 11216309HCID 11216309, compound

Product 1

HCID 10394361HCID 10394361, compoundYield 110.1%

Reagents, catalysts & solvents 1

HCID 70215362-Propanamine, 1-methoxy-, (2S)-Solvent

Conditions

Temperature
100 °C

Procedure

To N-(2-{5-tert-butyl-3-[(6-chloro-pyridine-3-carbonyl)-methanesulfonyl-amino]-2-methoxy-phenylcarbamoyl}-benzo[b]thiophen-7-yl)-6-chloro-nicotinamide (see Example 1) (33 mg) in a sealed tube was added (S)-(+)-1-methoxy-2-propylamine (150 μL). The reaction was purged with Ar and then heated to 100° C. in the sealed tube 12 h. The reaction mixture was cooled to room temperature and diluted with EtOAc, washed with NH4Cl solution, water, and brine. The organics were dried over MgSO4, filtered and concentrated down to give the crude product which was purified by flash chromatography on silica gel (CH2Cl2-2% MeOH/CH2Cl2) to give the title compound (16 mg, 53%) as a yellow foam.

Workup

  1. customThe reaction was purged with Ar
  2. temperatureThe reaction mixture was cooled to room temperature
  3. additiondiluted with EtOAc
  4. washwashed with NH4Cl solution, water, and brine
  5. dry with materialThe organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down
  8. customto give the crude product which
  9. customwas purified by flash chromatography on silica gel (CH2Cl2-2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-236175e8e4034877af5b086fad26e6eb
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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