Cyclopropylamine → HCID 9986150, compound

HRID 1986645Notes

Reaction equation

HRID 1986645 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].[CH:49]1([NH2:52])[CH2:51][CH2:50]1>>[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:52][CH:49]5[CH2:51][CH2:50]5)=[N:27][CH:26]=4)=[CH:20][CH:21]=[CH:22][C:16]=3[CH:15]=2)=[O:13])[CH:10]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 11216309HCID 11216309, compound

Product 1

HCID 9986150HCID 9986150, compoundYield 71%

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 200 μL of cyclopropylamine. The reaction was purged with Ar and heated to 100° C. in the sealed tube 12 h. The reaction mixture was cooled to room temperature and diluted with EtOAc, washed by NH4Cl solution, water, and brine. The organics were dried over MgSO4, filtered, concentrated down to give a residue which was purified by flash chromatography on silica gel (CH2Cl2-2% MeOH/CH2Cl2) to provide the title compound (21 mg, 71%), m.p. >264° C. dec.

Workup

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

Sources & evidence

ORD record
ord-e2391624c0fb4e9298b48989133fbb78
Source dataset
uspto-grants-2009_06
Patent number
US07550461B2

Reaction notes

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