Dimethylformamide → HCID 68982731, compound

HRID 1434838Notes

Reaction equation

HRID 1434838 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:30]=[C:29]([S:31]([CH3:33])=[O:32])[CH:28]=[CH:27][C:7]=1[C:8]([NH:10][C:11]1[C:12]([C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=2)=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:9].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Br[CH2:46][CH2:47][CH2:48][CH2:49]Br>CCOC(C)=O.O.CC#N>[ClH:26].[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([NH:19][C:17]([C:12]2[C:11]([NH:10][C:8](=[O:9])[C:7]3[CH:27]=[CH:28][C:29]([S:31]([CH3:33])=[O:32])=[CH:30][C:6]=3[O:5][CH2:4][CH2:3][CH2:2][N:1]3[CH2:49][CH2:48][CH2:47][CH2:46]3)=[CH:16][CH:15]=[CH:14][N:13]=2)=[O:18])=[N:21][CH:22]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 57936571HCID 57936571, compound

Product 1

HCID 68982731HCID 68982731, compoundYield 72.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 3-[2-(3-aminopropoxy)-4-methylsulfinyl-benzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (650 mg, 1.33 mmol), DMF (10 mL) and K2CO3 (552 mg, 4.0 mmol) was added 1,4-dibromobutane (0.16 mL, 1.33 mmol) and the mixture was heated to 80° C. for 5 h. The reaction mixture was cooled, diluted with EtOAc and water, and partitioned. The organic layer was concentrated and chromatographed (250 g of SiO2, CH2Cl2 to 5% of 2 M NH3/MeOH in CH2Cl2) to give impure product. This material was HPLC on a Vydac C18 column [5% CH3CN/(0.1% TFA in H2O) to 70% CH3CN/(0.1% TFA in H2O); Rt: 26.1 m] to give the desired product as a white solid (279 mg, 36%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned
  3. concentrationThe organic layer was concentrated
  4. customchromatographed (250 g of SiO2, CH2Cl2 to 5% of 2 M NH3/MeOH in CH2Cl2)
  5. customto give impure product

Sources & evidence

ORD record
ord-7d2b9b5b9f1a49c7a98e58cd25d39690
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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