HCID 178420200, compound → HCID 178419852, compound

HRID 2047541Notes

Reaction equation

HRID 2047541 reaction equation
[N:1]1([C@H:7]2[CH2:10][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([C:20]5[CH:21]=[N:22][N:23](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:24]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)=O>[N:1]1([C@H:7]2[CH2:8][C@H:9]([C:11]3[S:12][C:13]4[CH:19]=[C:18]([C:20]5[CH:24]=[N:23][NH:22][CH:21]=5)[CH:17]=[CH:16][C:14]=4[N:15]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 178420200HCID 178420200, compound

Product 1

HCID 178419852HCID 178419852, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The product of Example 51A (135.0 mg, 0.23 mmole) was dissolved in formic acid (88%, 2 ml) and stirred at room temperature for 2 hours. The reaction mixture concentrated was under reduced pressure. The solid residue was then treated with saturated aqueous sodium bicarbonate and extracted with dichloromethane (4×5 ml). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to give the crude product which was purified by column chromatography (1% ammonium hydroxide and 10% methanol in dichloromethane) to give 71.2 mg (90.5%) of title compound. MS: (M+H)+=339.

Workup

  1. concentrationThe reaction mixture concentrated
  2. additionThe solid residue was then treated with saturated aqueous sodium bicarbonate
  3. extractionextracted with dichloromethane (4×5 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product which
  9. customwas purified by column chromatography (1% ammonium hydroxide and 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-9e63c44676d7431b97f124cc1f8d5aa2
Source dataset
uspto-grants-2013_11
Patent number
US08592467B2

Reaction notes

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