HCID 86689246, compound → HCID 86689245, compound

HRID 1409508Notes

Reaction equation

HRID 1409508 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[O:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:19]=[CH:18][C:17]3[O:20][C:21]4[C:26]([C:27]5([C:35]6[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=6)[C:29]([NH2:36])=[N:28]5)[C:16]=3[CH:15]=2)=[CH:25][C:24]([C:37]2[C:38]([F:43])=[N:39][CH:40]=[CH:41][CH:42]=2)=[CH:23][CH:22]=4)[CH2:10][CH2:9]1>CO>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:43][C:38]1[C:37]([C:24]2[CH:25]=[C:26]3[C:27]4([C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:29]([NH2:36])=[N:28]4)[C:16]4[CH:15]=[C:14]([CH:11]5[CH2:12][CH2:13][O:8][CH2:9][CH2:10]5)[N:19]=[CH:18][C:17]=4[O:20][C:21]3=[CH:22][CH:23]=2)=[CH:42][CH:41]=[CH:40][N:39]=1

Participants

3

Reactant 1

HCID 86689246HCID 86689246, compound

Product 1

HCID 86689245HCID 86689245, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A flask containing a solution of 3-(3,6-dihydro-2H-pyran-4-yl)-7-(2-fluoropyridin-3-yl)spiro[chromeno[2,3-c]pyridine-5,1′-isoindol]-3′-amine 2,2,2-trifluoroacetate (30 mg, 0.051 mmol) and MeOH (4 mL) was evacuated and backfilled with nitrogen. Pd/C (10 weight %, 100 mg, Aldrich) was added and the flask was evacuated and backfilled with H2 gas. The flask was fitted with a balloon filled with H2 gas (1 atm) and the reaction mixture was stirred at RT for 3 h. The reaction mixture was filtered through a pad of celite and the celite was washed with EtOAc. The solvent was removed under reduced pressure and the remaining residue was purified by reversed-phase preparative HPLC using a Phenomenex Gemini column, 10 micron, C18, 110 Å, 100×50 mm, 0.1% TFA in CH3CN/H2O, gradient 10% to 100% over 20 min to obtain the title compound (7.8 mg, 25.9%) as a white solid.

Workup

  1. customwas evacuated
  2. additionPd/C (10 weight %, 100 mg, Aldrich) was added
  3. customthe flask was evacuated
  4. customThe flask was fitted with a balloon
  5. additionfilled with H2 gas (1 atm)
  6. filtrationThe reaction mixture was filtered through a pad of celite
  7. washthe celite was washed with EtOAc
  8. customThe solvent was removed under reduced pressure
  9. customthe remaining residue was purified by reversed-phase preparative HPLC
  10. customover 20 min

Sources & evidence

ORD record
ord-4df67ac93a094d71a14caf3675ee435f
Source dataset
uspto-grants-2014_12
Patent number
US08921363B2

Reaction notes

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