Water → HCID 68350894, compound

HRID 1501591Notes

Reaction equation

HRID 1501591 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH2:9][C:10]([CH3:17])([CH3:16])[NH:11][C:12]([CH3:15])([CH3:14])[CH:13]=2)=[N:6][C:5]2[N:18]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:20][C:4]=2[C:3]=1[C:24]([OH:26])=O.[NH2:27][CH2:28][C:29]1[C:30](=[O:37])[NH:31][C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>CS(C)=O.CO.C(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH2:9][C:10]([CH3:17])([CH3:16])[NH:11][C:12]([CH3:14])([CH3:15])[CH:13]=2)=[N:6][C:5]2[N:18]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:20][C:4]=2[C:3]=1[C:24]([NH:27][CH2:28][C:29]1[C:30](=[O:37])[NH:31][C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])=[O:26]

Participants

7

Reactant 4

HCID 962WaterHCID 2724699PyBOPHCID 70638443-(Aminomethyl)-4,6-dimethyl-1,2-dihydropyridin-2-oneHCID 68294961HCID 68294961, compound

Product 1

HCID 68350894HCID 68350894, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 5-chloro-1-isopropyl-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid (0.07 g, 0.18 mmol) and 3-(aminomethyl)-4,6-dimethylpyridin-2(1H)-one (0.056 g, 0.372 mmol) in DMSO (1 mL) and was stirred at room temperature for 15 min. Then PyBOP (0.145 g, 0.279 mmol) was added to it and stirring was continued for 12 h. After completion of the reaction, water was added to it and extraction was carried out using 10% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by prep. HPLC to give the desired compound (26% yield). LCMS: 511.20 (M+1)+; HPLC: 91.79% (@ 254 nm) (Rt; 4.914); 1H NMR (DMSO-d6, 400 MHz) δ 11.55 (s, 1H), 8.74 (d, 3H, J=4 Hz), 8.05 (s, 1H), 6.06 (s, 1H), 5.89 (s, 1H), 5.15-5.08 (m, 1H), 4.36 (d, 2H, J=4.8 Hz), 2.59 (s, 2H), 2.23 (s, 3H), 2.11 (s, 3H), 1.54 (s, 6H), 1.49 (s, 6H), 1.48 (d, 6H, J=7.6 Hz).

Workup

  1. additionwas added to it and extraction
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford crude material which
  7. customwas purified by prep

Sources & evidence

ORD record
ord-453cc69391364c7a93a4f22997740bcb
Source dataset
uspto-grants-2015_12
Patent number
US09206157B2

Reaction notes

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