Diisopropylcarbodiimide → HCID 70817358, compound

HRID 402468Notes

Reaction equation

HRID 402468 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:15][CH2:16][C:17](O)=[O:18])=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:5]2[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3]1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[C:45]1([C@H:51]([CH3:54])[CH2:52][NH2:53])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C>[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:15][CH2:16][C:17]([NH:53][CH2:52][C@H:51]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH3:54])=[O:18])=[CH:9][C:10]([C:11]([F:14])([F:12])[F:13])=[C:5]2[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3]1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1547950(2S)-2-Phenylpropan-1-amineHCID 67209383(1-Methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid

Product 1

HCID 70817358HCID 70817358, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (1-Methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (100 mg, 0.28 mmol), DIC (53 mg, 0.42 mmol) and HOBt (49 mg, 0.36 mmol) in DMF (5 ml) was stirred at rt for 10 min. (S)-(+)-2-Phenyl-propylamine (42 mg, 0.31 mmol) was added to the reaction mixture at rt and stirring was continued overnight at rt. After completion of the reaction, ice-cold water (10 mL) was added to the reaction mixture and the mixture was stirred for 20 min. The reaction mixture was extracted with diethyl ether, dried over sodium sulfate and concentrated under reduced pressure. The solid was triturated with pentane (20 ml×3) followed by hexane (15 ml) to yield the title compound as white solid. (100 mg, 75%). Mp=91-93° C. [1H-NMR (CDCl3, 300 MHz) δ 7.63-7.42 (m, 5H), 7.20-6.92 (m, 5H), 6.80 (s, 1H), 6.18-6.12 (m, 1H), 4.92 (dd, 2H), 4.1 (s, 3H), 3.81-3.68 (m, 1H), 3.40-3.33 (m, 1H), 2.98-2.90 (m, 1H), 1.41 (d, 3H); HPLC RtA=6.325 min. (98%); LCMS RtA=1.835, [M+H]+=469.1]

Workup

  1. additionwas added to the reaction mixture at rt
  2. additionwas added to the reaction mixture
  3. stirringthe mixture was stirred for 20 min
  4. extractionThe reaction mixture was extracted with diethyl ether
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe solid was triturated with pentane (20 ml×3)

Sources & evidence

ORD record
ord-d2cab156859f496587768171abc6d3ec
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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