Triethylamine → HCID 86686153, compound

HRID 1409692Notes

Reaction equation

HRID 1409692 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[Br:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=O)=[CH:26][N:25]=1.C(N(CC)CC)C.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([NH:53][CH:54]2[CH2:56][CH2:55]2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41]>CN(C)C=O.C(OCC)(=O)C.O>[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][CH:50]([N:53]([C:28]([C:27]2[CH:26]=[N:25][C:24]([Br:23])=[CH:32][CH:31]=2)=[O:30])[CH:54]2[CH2:55][CH2:56]2)[CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:41])[CH3:42]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2389326-Bromonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2769591tert-Butyl 4-(cyclopropylamino)piperidine-1-carboxylate

Product 1

HCID 86686153HCID 86686153, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (2.80 g) is added to a mixture of 6-bromo-nicotinic acid (1.85 g) and triethylamine (1.28 mL) in N,N-dimethylformamide (25 mL) cooled in an ice bath. The mixture is stirred for 30 min prior to the addition of a solution of 4-cyclopropylamino-piperidine-1-carboxylic acid tert-butyl ester (2.00 g) in N,N-dimethylformamide (5 mL). The resulting mixture is stirred at room temperature over night. Water and ethyl acetate are added and the organic phase is separated, washed with water, 1N aqueous NaOH solution, and brine, and dried over MgSO4. The solvent is evaporated in vacuo and the residue is triturated with diisopropyl ether to yield the title compound. LC (method 5): tR=1.59 min; Mass spectrum (ESI+): m/z=424/426 (Br) [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. stirringThe resulting mixture is stirred at room temperature over night
  3. customthe organic phase is separated
  4. washwashed with water, 1N aqueous NaOH solution, and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent is evaporated in vacuo
  7. customthe residue is triturated with diisopropyl ether

Sources & evidence

ORD record
ord-3152d3ee75b2455caf43f4f4ce625ef9
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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