Cyclopropanemethanol → HCID 86715115, compound

HRID 533926Notes

Reaction equation

HRID 533926 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.C1C=[CH:13][C:14]2N(O)N=N[C:15]=2[CH:16]=1.CCN(C(C)C)C(C)C.C1(CO)CC1>O.C(Cl)CCl.CN(C=O)C>[CH:15]1([CH2:16][O:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)=[O:10])[CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 75644CyclopropanemethanolHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 86715115HCID 86715115, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To DMF (10 mL) was added 5-hydroxy-pyridine-2-carboxylic acid (1.0 g) followed by EDC (1.38 g), HOBt (971 mg) and DIPEA (1.22 mL). After 15 minutes cyclopropyl-methanol (520 mg) was added. After 12 hours the mixture was diluted with water and extracted three times with EA. The combined organic phases were washed with brine, dried (Na2SO4) and concentrated to provide the title compound. MS ESI+: m/z=194 [M+H]+.

Workup

  1. extractionextracted three times with EA
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-59713c3d604049228389085ec6c7dc2c
Source dataset
uspto-grants-2014_10
Patent number
US08853412B2

Reaction notes

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