Borane,N-dimethylmethanamine (1:1) → HCID 21906555, compound

HRID 988620Notes

Reaction equation

HRID 988620 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:16]=[CH:17][CH:18]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]2)=[N:6][CH:7]=1.[B-][N+](C)(C)C>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:31])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 21906225HCID 21906225, compound

Product 1

HCID 21906555HCID 21906555, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution containing N-(5-chloropyridin-2-yl)-2-(1-Boc-piperidin-4-yl-methylidene)aminobenzamide (1.35 g, 3.05 mmol) and borane trimethylamine complex (667 mg, 9.14 mmol) in glacial acetic acid (50 mL) was heated at reflux for 2 h. The mixture was concentrated and the residue was dissolved in methanol and 12 N HCl. After 24 h, the mixture was concentrated, the residue was dissolved in 2 N ammonia in methanol and concentrated. The residue was triturated from methanol:EtOAc yielding 1.03 g (98%) of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in methanol
  5. concentrationthe mixture was concentrated
  6. dissolutionthe residue was dissolved in 2 N ammonia in methanol
  7. concentrationconcentrated
  8. customThe residue was triturated from methanol

Sources & evidence

ORD record
ord-a4ba57872f254e82882c52e4f4c4bd77
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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