Water → HCID 70816893, compound

HRID 402490Notes

Reaction equation

HRID 402490 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:17])[N:3]=1.CN(C(ON1N=N[C:28]2[CH:29]=[CH:30][CH:31]=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CC[N:44]([CH:48]([CH3:50])[CH3:49])C(C)C.O.[CH3:52]N(C=O)C>>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([O:12][CH2:13][C:14]([NH:44][C@H:48]([C:49]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[CH3:52])[CH3:50])=[O:16])=[CH:8][C:9]=2[CH3:11])[N:4]([CH3:17])[N:3]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67209443HCID 67209443, compound

Product 1

HCID 70816893HCID 70816893, compoundYield 50%

Procedure

To a solution of 2-((3-chloro-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yl)oxy)acetic acid in DMF (5 ml) was added HATU (1.03 g, 2.72 mmol) and DIPEA (1.2 ml, 6.81 mmol). After 20 min at rt, (S)-1-(p-tolylethan)amine (0.43 ml, 2.95 mmol) was added to the mixture. After 16 h, water was added and the mixture extracted with CH2Cl2. The organic phases were dried over Na2SO4 and the solvent removed under reduced pressure. Purification by column chromatography (eluent 60% hexane in EtOAc) yielded 420 mg (50%) of the title compound. [1H-NMR (DMSO-d6, 600 MHz) δ 8.51 (d, 1H), 7.16 (d, 2H), 7.05 (d, 2H), 6.63 (s, 1H), 4.93 (t, 1H), 4.83 (d, 1H), 4.79 (d, 1H), 3.77 (s, 3H), 2.60 (s, 3H), 2.25 (s, 3H), 1.35 (d, 3H); HPLC-MS RtJ=1.15 min; [M+H]+=373.1, 375.1]

Workup

  1. waitAfter 16 h
  2. extractionthe mixture extracted with CH2Cl2
  3. dry with materialThe organic phases were dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customPurification by column chromatography (eluent 60% hexane in EtOAc)

Sources & evidence

ORD record
ord-bc4bb9973cbb4b99badfa1439097eaeb
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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