Pyridine → HCID 123168409, compound

HRID 626344Notes

Reaction equation

HRID 626344 reaction equation
N[CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:19]([NH:21][C:22]3[CH:23]=[C:24](/[CH:29]=[CH:30]/[C:31]([O:33]CC)=[O:32])[CH:25]=[CH:26][C:27]=3[F:28])=[O:20])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=[CH:7][CH:8]=1.C(OC(=O)C)(=[O:38])C.N1C=CC=CC=1.[C:49](#[N:51])[CH3:50]>>[C:49]([NH:51][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([C:19]([NH:21][C:22]3[CH:23]=[C:24]([CH:29]=[CH:30][C:31]([OH:33])=[O:32])[CH:25]=[CH:26][C:27]=3[F:28])=[O:20])[C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=[CH:7][CH:8]=1)(=[O:38])[CH3:50]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 7918Acetic AnhydrideHCID 117951652HCID 117951652, compound

Product 1

HCID 123168409HCID 123168409, compound

Procedure

Compound 16d (600 mg crude) was dissolved in acetonitrile (15 mL), acetic anhydride (1 mL) and pyridine (1 mL) were added to the reaction mixture and stirred at rt for 16 h. The reaction mixture was evaporated to dryness. To the crude was added THF/water (1:1, 50 mL) followed by lithium hydroxide 1.5 g and the reaction was stirred at rt for 16 h. The reaction mixture was concentrated under vacuum to dryness. The resulting residue was adjusted to pH 5 with dilute HCl and the resulting suspension was stirred for some time following which the solid formed was filtered, dried under vacuum and purified by reverse phase HPLC.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionTo the crude was added THF/water (1:1, 50 mL)
  3. stirringthe reaction was stirred at rt for 16 h
  4. concentrationThe reaction mixture was concentrated under vacuum to dryness
  5. stirringthe resulting suspension was stirred for some time
  6. customformed
  7. filtrationwas filtered
  8. customdried under vacuum
  9. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-2d438916ca704aa7bc1f946d235619cb
Source dataset
uspto-grants-2016_04
Patent number
US09309187B2

Reaction notes

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