Acetic Acid → HCID 57911418, compound

HRID 1099189Notes

Reaction equation

HRID 1099189 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[O:5]=[C:6]1[NH:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C@H:24]2[C:30]3=[N:31][C:32](N)=[CH:33][CH:34]=[C:29]3[CH2:28][C@H:27]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=3[F:43])[CH2:26][CH2:25]2)=[O:22])[CH2:17][CH2:16]1.C=O.[C:46](O)(=O)C>C(#N)C>[O:5]=[C:6]1[NH:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]1[CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C@H:24]2[C:30]3=[N:31][C:32]([N:2]([CH3:1])[CH3:46])=[CH:33][CH:34]=[C:29]3[CH2:28][C@H:27]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[C:37]=3[F:43])[CH2:26][CH2:25]2)=[O:22])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57911461HCID 57911461, compound

Product 1

HCID 57911418HCID 57911418, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

SODIUM CYANOBOROHYDRIDE (108 mg, 1.721 mmol) was added to the Acetonitrile (2 mL) solution of (6R,9R)-2-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (46 mg, 0.086 mmol) and FORMALDEHYDE (1 mL, 13.43 mmol) at rt. The reaction was stirred at room temperature for 4 hours. ACETIC ACID (0.5 mL, 8.73 mmol) was added to the reaction mixture and the reaction was stirred overnight. Volatile was removed mostly via vacuum and the crude was added NaOH (1N) and stirred at room temperature for 1 hour before extract with ethyl acetate. The ethyl acetate layer was dried (Na2SO4), filtered and concentrated. Flash column by methanol in CH2Cl2 from 0 to 4% to 8% gave the desired product (19.8 mg, 39%). MS (ESI)[M+H+]=563.42.

Workup

  1. stirringthe reaction was stirred overnight
  2. customVolatile was removed mostly via vacuum
  3. additionthe crude was added NaOH (1N)
  4. stirringstirred at room temperature for 1 hour
  5. extractionbefore extract with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-37cbd92f23b14fc5a781b510dce0f5a2
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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