4-Bromobutyryl chloride → HCID 89560485, compound

HRID 590392Notes

Reaction equation

HRID 590392 reaction equation
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)=[CH:7][CH:6]=1)[NH2:4].CCN(C(C)C)C(C)C.[Br:28][CH2:29][CH2:30][CH2:31][C:32](Cl)=O>C(Cl)Cl>[Br:28][CH2:29][CH2:30][CH2:31][C:32]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[CH:7][C:8]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)=[CH:9][CH:10]=2)[N:4]=1

Participants

5

Reactant 3

HCID 702254-Bromobutyryl chlorideHCID 81531DiisopropylethylamineHCID 73853505HCID 73853505, compound2×

Product 1

HCID 89560485HCID 89560485, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of N′-hydroxy-4-[(tetrahydro-2H-pyran-2-yloxy)methyl]benzenecarboximidamide (Intermediate 27; 211 mg, 0.84 mmol) in DCM (3 mL) was added DIEA (0.176 mL, 1.01 mmol). The mixture was cooled to 0° C. and a solution of 4-bromobutanoyl chloride (0.108 mL, 0.88 mmol) in DCM (1 mL) was added dropwise. The mixture was stirred overnight at room temperature. The solvent was removed under reduced pressure and the crude obtained was purified by column chromatography with silica gel, eluting with a mixture of Hexane:ether give the title compound as a solid (198 mg, 53%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude obtained
  3. customwas purified by column chromatography with silica gel
  4. washeluting with a mixture of Hexane

Sources & evidence

ORD record
ord-234aa57425cb453e9e11efb391c4d6c8
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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