Dimethylamine → HCID 19608542, compound

HRID 1602931Notes

Reaction equation

HRID 1602931 reaction equation
CNC.N(CC#CC[N:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([O:17][CH2:18][C:19]2[C:27]3[O:26][CH:25]=[CH:24][C:23]=3[CH:22]=[C:21]([C:28]3[N:32]([CH3:33])[N:31]=[N:30][CH:29]=3)[CH:20]=2)[C@@H:12]1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[N+]=[N-]>O1CCOCC1>[C:34]1([CH:12]2[CH:13]([O:17][CH2:18][C:19]3[C:27]4[O:26][CH:25]=[CH:24][C:23]=4[CH:22]=[C:21]([C:28]4[N:32]([CH3:33])[N:31]=[N:30][CH:29]=4)[CH:20]=3)[CH2:14][CH2:15][CH2:16][NH:11]2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 57289013HCID 57289013, compound

Product 1

HCID 19608542HCID 19608542, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

Dimethylamine (approximately 10 ml) was condensed at -80° C. in a pressure tube and to this was added a solution of (2S,3S]-1-(4-azidobut-2-yn-1-yl)-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine (120 mg) in dioxan (5 ml). The tube was sealed and the solution was heated at 80° C. for 14 hours. The solvent was evaporated under reduced pressure to dryness and the residue was purified by MPLC [5% methanol in dichloromethane containing 0.25% ammonia (SG. 0.88)] to give [2S,3S]-1-[(5-dimethylaminomethyl)-1H[1,2,3]-triazol-4-yl)methyl]-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine as a clear oil (47 mg). To a solution of this residue in diethyl ether was added 5M-HCl in ethanol. The solution was evaporated to dryness and the residue recrystallised from ether/ethanol to give [2S,3S]-1-[(5-(Dimethylaminomethyl)-1H-[1,2,3]triazol-4-yl)methyl]-2-phenyl-3-[(5-(1-methyl-1H-[1,2,3]triazol-5-yl)benzofuran-7-yl)methyloxy]piperidine hydrochloride (57 mg) mp 136-138° C. 1H NMR (360 MHz,D2O)δ1.64 (1H, m), 1.87 (1H, m), 2.34 (2H, m), 2.65 (6H, s), 3.27 (1H, d, J=14.0 Hz), 3.71-3.78 (3H, m), 3.85 (1H, br s), 3.93 (3H, s), 4.24 (1H, s), 4.33 (1H, d, J=16.0 Hz), 4.38 (1H, d, J=16.0 Hz), 4.69 (1H, d, J=14.0 Hz), 5.00 (1H, d, J=14.0 Hz), 6.79 (1H, s), 6.92 (1H, d, J=1.0 Hz), 7.16 (5H, m), 7.63 (1H, s), 7.74 (1H, s), 7.81 (1H, d, J=1.0 Hz); m/z (CI+) 527 (M+H+).

Workup

  1. customcondensed at -80° C. in a pressure tube
  2. customThe tube was sealed
  3. customThe solvent was evaporated under reduced pressure to dryness
  4. customthe residue was purified by MPLC [5% methanol in dichloromethane containing 0.25% ammonia (SG. 0.88)]

Sources & evidence

ORD record
ord-b7808b6989bd427ba6ff53a3bea0e07e
Source dataset
uspto-grants-1999_11
Patent number
US05985896

Reaction notes

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