3,4-dihydro-2H-pyran → HCID 67469573, compound

HRID 1522632Notes

Reaction equation

HRID 1522632 reaction equation
[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([CH2:12][C@@H:13]([OH:15])[CH3:14])[N:11]=2)[N:5]=[CH:6][C:7]=1[F:8].[Cl:16][C:17]1[C:22]([F:23])=[CH:21][N:20]=[C:19]2[CH:24]=[N:25][N:26]([CH2:27][C@@H:28]([OH:30])[CH3:29])[C:18]=12.[O:31]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32]1>C1COCC1>[Cl:16][C:17]1[C:22]([F:23])=[CH:21][N:20]=[C:19]2[CH:24]=[N:25][N:26]([CH2:27][C@@H:28]([O:30][CH:32]3[CH2:33][CH2:34][CH2:35][CH2:36][O:31]3)[CH3:29])[C:18]=12.[Cl:1][C:2]1[C:3]2[C:4](=[CH:9][N:10]([CH2:12][C@@H:13]([O:15][CH:19]3[CH2:18][CH2:17][CH2:22][CH2:21][O:31]3)[CH3:14])[N:11]=2)[N:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 67469585HCID 67469585, compoundHCID 67470412HCID 67470412, compound

Product 2

HCID 67469573HCID 67469573, compoundHCID 67470422HCID 67470422, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-(7-chloro-6-fluoro-2H-pyrazolo[4,3-b]pyridin-2-yl)propan-2-ol and (S)-1-(7-chloro-6-fluoro-1H-pyrazolo[4,3-b]pyridin-1-yl)propan-2-ol in THF (10 mL) was added 3,4-dihydro-2H-pyran (0.332 mL, 3.66 mmol) and p-TSA monohydrate (580 mg, 3.05 mmol) and the mixture was stirred at room temperature for 3 hours and then concentrated to give a residue which was purified on silica gel column chromatography eluted with dichloromethane/Methanol (0-10%) to give 7-chloro-6-fluoro-1-((2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-pyrazolo[4,3-b]pyridine and 7-chloro-6-fluoro-2-((2S)-2-(tetrahydro-2H-pyran-2-yloxy)propyl)-2H-pyrazolo[4,3-b]pyridine which were used in next step. MS [M+H] found 314.3.

Workup

  1. concentrationconcentrated
  2. customto give a residue which
  3. customwas purified on silica gel column chromatography
  4. washeluted with dichloromethane/Methanol (0-10%)

Sources & evidence

ORD record
ord-a9db5a341ae74252b68fc00942998d2f
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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