Selectfluor → HCID 67238123, compound

HRID 711508Notes

Reaction equation

HRID 711508 reaction equation
[CH2:1]([O:3][CH2:4][C@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:11]2[C:22](=[O:25])[NH:23][CH2:24][C:10]=2[CH:9]=1)[CH3:2].[B-](F)(F)(F)[F:35].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1>C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:3][CH2:4][C@H:5]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=2)[C:11]2[C:22](=[O:25])[NH:23][CH2:24][C:10]=2[C:9]=1[F:35])[CH3:2]

Participants

5

Reactant 2

HCID 2724933SelectfluorHCID 67239348HCID 67239348, compound

Product 1

HCID 67238123HCID 67238123, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a chilled solution of (R)-tert-butyl 1-ethoxy-3-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)propan-2-ylcarbamate (94.7 mg, 0.208 mmol) in CH2Cl2 (5 mL) at 0° C. was added SELECTFLUOR® (73.6 mg, 0.208 mmol). The mixture was left stirring in an ice bath and warmed slowly to RT for 6 h. Afterwards, the mixture was diluted with EtOAc (10 mL) and washed with saturated aq NaHCO3 (5 mL) followed by water (5 mL) and brine (5 mL). The organic layers were combined, dried over Na2SO4, and concentrated to a brown residue. The resulting crude material was reconstituted in MeOH/DCM (5 mL) and purified via preparative HPLC. The collected fractions were collected and ACN was removed via rotary evaporation. The resulting aq solution was neutralized with saturated aq NaHCO3 and washed with EtOAc (2×200 mL), dried over Na2SO4, filtered, and the organic phase stripped to dryness via rotary evaporation to yield the title compound. [M+H] calc'd for C24H32FN5O4, 474. found, 474.

Workup

  1. waitThe mixture was left
  2. washwashed with saturated aq NaHCO3 (5 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to a brown residue
  5. custompurified via preparative HPLC
  6. customThe collected fractions were collected
  7. customACN was removed via rotary evaporation
  8. washwashed with EtOAc (2×200 mL)
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customthe organic phase stripped to dryness via rotary evaporation

Sources & evidence

ORD record
ord-f79d5b46845d440487b8a160b8007cb5
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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