Pentylamine → HCID 10383166, compound

HRID 228415Notes

Reaction equation

HRID 228415 reaction equation
[F:1][C:2]1[C:17]([F:18])=[C:16]([CH:19]=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1.[CH2:21]([NH2:26])[CH2:22][CH2:23][CH2:24][CH3:25].[BH4-].[Na+]>CO>[F:1][C:2]1[C:17]([F:18])=[C:16]([CH2:19][NH:26][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 8060PentylamineHCID 4311764Sodium borohydrideHCID 59730256HCID 59730256, compound

Product 1

HCID 10383166HCID 10383166, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 6-(2,3-difluoro-4-formyl-phenoxy)-nicotinamide (278 mg, 1.00 mmol), n-pentylamine (105 mg, 1.20 mmol), and MeOH (3 ml) in a round bottom flask equipped with nitrogen inlet and stir for two hours. Add NaBH4 (57 mg, 1.50 mmol) and stir for an additional two hours before concentrating. Dissolve concentrate in EtOAc and wash with 5% aq. KOH and brine, dry (Na2SO4), and concentrate. Purify on silica gel (5% (1 M NH3/MeOH)/DCM) to give the title compound (290 mg) as a white solid. Mass spectrum (ion spray): m/z=350 (M+1); 1HNMR (DMSO-d6): 8.55 (s, 1H), 8.28 (d, 1H), 8.03 (s, 1H), 7.50 (s, 1H), 7.29 (m, 1H), 7.22 (d, 1H), 7.15 (m, 1H), 3.73 (s, 2H), 2.48 (t, 2H), 1.41 (m, 2H), 1.25 (m, 4H), 0.84 (m, 3H).

Workup

  1. concentrationbefore concentrating
  2. dissolutionDissolve
  3. concentrationconcentrate in EtOAc
  4. washwash with 5% aq. KOH and brine
  5. dry with materialdry (Na2SO4)
  6. concentrationconcentrate
  7. customPurify on silica gel (5% (1 M NH3/MeOH)/DCM)

Sources & evidence

ORD record
ord-e09a0261f1174a0bb6637765fc73acc3
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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