Diisopropylcarbodiimide → HCID 69915134, compound

HRID 402476Notes

Reaction equation

HRID 402476 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]([OH:15])=O)=[CH:9][CH:10]=[C:5]2[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:3]1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:41][C@H:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>CN(C=O)C>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:11][CH2:12][C:13]([NH:49][C@H:42]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH3:41])=[O:15])=[CH:9][CH:10]=[C:5]2[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:3]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 758181-Phenethylamine, (-)-HCID 67209460HCID 67209460, compound

Product 1

HCID 69915134HCID 69915134, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(1-methyl-3-phenyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetic acid (0.14 g, 0.494 mmol), DIC (0.094 g, 0.744 mmol) and HOBt (0.087 g mg, 0.644 mmol) in DMF (4.0 ml) was stirred at rt for 15 min. (S)-(−)-α methyl benzyl amine (0.072 g, 0.594 mmol) was added to the reaction mixture at rt and stirring was continued overnight. The reaction mixture was concentrated. Diethyl ether was added and the mixture was washed with water, followed by brine and dried over Na2SO4. Concentration of the organic layer furnished the crude product as an off-white solid. The product was purified by preparative HPLC using acetonitrile/water as mobile phase to yield the title compound as a white solid (0.133 g, 68%). [1H-NMR (CDCl3, 300 MHz) δ 8.22 (d, 1H), 7.96-7.89 (m, 2H), 7.55-7.38 (m, 3H), 7.37-7.21 (m, 5H), 6.73 (d, 1H), 6.61 (d, 1H), 5.35-5.21 (m, 1H), 4.99 (s, 2H), 4.03 (s, 3H), 1.53 (d, 3H); HPLC RtA=5.273 min (98%) LCMS RtE=1.921 min; [M+H]+=387.1; Mp=55-56° C.]

Workup

  1. additionwas added to the reaction mixture at rt
  2. concentrationThe reaction mixture was concentrated
  3. additionDiethyl ether was added
  4. washthe mixture was washed with water
  5. dry with materialdried over Na2SO4
  6. customConcentration of the organic layer furnished the crude product as an off-white solid
  7. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-d4a174cd89fa4bcda5dd11af0444568f
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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