Dimethylformamide → HCID 22175150, compound

HRID 1059683Notes

Reaction equation

HRID 1059683 reaction equation
[CH:1]1([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ON1C2C=CC=CC=2N=N1.[CH3:24]CN=C=NCCCN(C)C.C[N:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.CN([CH:45]=[O:46])C>O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH:11][C:45]([C:41]3[C:40]([OH:39])=[CH:24][CH:38]=[CH:37][N:36]=3)=[O:46])=[CH:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 807644-Cyclohexylbenzenamine

Product 1

HCID 22175150HCID 22175150, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 3-hydroxypyridine-2-carboxylic acid (obtained from 16 by catalytic hydrogenation in the presence of Pd/C as described earlier) (0.42 g, 3 mmol) and 4-cyclohexylaniline (0.35 g, 2 mmol) in dry DMF (5 mL) were successively added 1-hydroxybenzotriazole (0.48 g), EDCI (0.65 g) and N-methylmorpholine (1.41 g). An additional amount of DMF (5 mL) was added and the reaction mixture stirred at room temperature overnight. The mixture was poured into water (200 mL), then extracted with EtOAc (2×75 mL). The organic extracts were combined, washed with water (100 mL), and saturated NaCl solution (50 mL), dried (MgSO4) and concentrated. The crude oil which solidified upon standing was chromatographed on silica gel (4:1 petroleum ether-EtOAc) to give the title compound (0.42 g) as a tan solid, m.p. 91-93° C.

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washwashed with water (100 mL), and saturated NaCl solution (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customupon standing was chromatographed on silica gel (4:1 petroleum ether-EtOAc)

Sources & evidence

ORD record
ord-3c25288519a147d9917827383dec835f
Source dataset
uspto-grants-2003_02
Patent number
US06521622B1

Reaction notes

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