Selectfluor → HCID 86654708, compound

HRID 2092758Notes

Reaction equation

HRID 2092758 reaction equation
[O:1]=[C:2]1[C:6]2[C:7]([NH:26][C:27]3[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=3)=[N:8][C:9]([NH:11][C@@H:12]3[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]3[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:10][C:5]=2[CH2:4][NH:3]1.[B-](F)(F)(F)[F:35].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>>[F:35][C:10]1[C:5]2[CH2:4][NH:3][C:2](=[O:1])[C:6]=2[C:7]([NH:26][C:27]2[CH:28]=[C:29]([CH3:33])[CH:30]=[CH:31][CH:32]=2)=[N:8][C:9]=1[NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 2724933SelectfluorHCID 86654728HCID 86654728, compound

Product 1

HCID 86654708HCID 86654708, compoundYield 46%

Procedure

A solution of tert-butyl (1S,2R)-2-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)cyclohexylcarbamate (94 mg, 0.208 mmol) and SELECTFLUOR® (73.7 mg, 0.208 mmol) was stirred at 0° C. for 5 h and at RT for 1 h. The mixture was filtered and the filtrate was purified by preparative HPLC. The fractions were collected and concentrated. The residue was washed with saturated aq NaHCO3 solution, extracted with EtOAc, washed with brine, dried over MgSO4, and evaporated to give the title compound as yellow solid (45 mg, 46.0%). [M+H] calc'd for C25H32FN5O3, 470. found, 470.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was purified by preparative HPLC
  3. customThe fractions were collected
  4. concentrationconcentrated
  5. washThe residue was washed with saturated aq NaHCO3 solution
  6. extractionextracted with EtOAc
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. customevaporated

Sources & evidence

ORD record
ord-6dd950b92e604b5d9672f92b91215c58
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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