Dimethylformamide → HCID 68456995, compound

HRID 502331Notes

Reaction equation

HRID 502331 reaction equation
[N:1]1([C:6]([C:8]2[CH:16]=[CH:15][C:11](C(O)=O)=CN=2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.C1N=CN([C:22](N2C=NC=C2)=[O:23])C=1.[Cl:29][C:30]1[CH:43]=[CH:42][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([NH2:41])[CH2:37][CH2:36]2)=[CH:32][C:31]=1[O:44][CH2:45][CH3:46].C[N:48](C=O)C>>[Cl:29][C:30]1[CH:43]=[CH:42][C:33]([CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([NH:41][C:22](=[O:23])[C:15]3[CH:16]=[CH:8][C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[N:48][CH:11]=3)[CH2:37][CH2:36]2)=[CH:32][C:31]=1[O:44][CH2:45][CH3:46]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 682631,1'-CarbonyldiimidazoleHCID 592103771-(4-Chloro-3-ethoxybenzyl)piperidin-4-ylamineHCID 68457789HCID 68457789, compound

Product 1

HCID 68456995HCID 68456995, compoundYield 41%

Procedure

6-(1-Imidazoyl)nicotinic acid (21 mg, 0.11 mmol) and CDI (19 mg, 0.12 mmol) were dissolved in DMF (0.5 ml) and shaken for 1 h. Then 1-(4-chloro-3-ethoxy-benzyl)piperidin-4-ylamine (27 mg, 0.1 mmol) was added as a solution in DMF (0.5 ml) was added and the reaction stirred for 16 h, after which time the solvent was evaporated and the residue purified by reversed phase HPLC (MeCN:H2O) affording the title compound (18 mg, 41%). MS: 440.4 (MH+)

Workup

  1. additionwas added
  2. stirringthe reaction stirred for 16 h
  3. customafter which time the solvent was evaporated
  4. customthe residue purified by reversed phase HPLC (MeCN:H2O)

Sources & evidence

ORD record
ord-efd28a27cbfc46d3858891ada0f93ea0
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

Loading…