Ammonia → HCID 22258723, compound

HRID 412310Notes

Reaction equation

HRID 412310 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#N)=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:27][CH:26]=[CH:25][C:24]=2[O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)N=1.S([O-])([O-])(=O)=O.[NH4+:49].[NH4+:50].[NH3:51].[CH:52](OCC)(OCC)OCC>CCO>[NH2:49]/[CH:52]=[N:50]/[C:8]1[C:7]([C:2]#[N:1])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:23]2[C:28]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)=[CH:27][CH:26]=[CH:25][C:24]=2[O:39][CH2:40][CH:41]2[CH2:43][CH2:42]2)[N:51]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 31214Ethyl orthoformateHCID 6097028Ammonium SulfateHCID 22258972HCID 22258972, compound

Product 1

HCID 22258723HCID 22258723, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl 3-(2-amino-3-cyano-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)-1-piperidinecarboxylate (0.580 g, 0.999 mmol) in triethyl orthoformate (1.2 mL) was added ammonium sulfate (0.004 g, 0.030 mmol), and the mixture was stirred at 150° C. for 2 hrs. After cooled to room temperature, EtOH (1.5 mL) and a solution of NH3 in EtOH (8.6 N, 0.5 mL) were added successively. The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was triturated with hexane and isopropyl ether, and dried under reduced pressure to give tert-butyl 3-(2-{[(1E)-aminomethylidene]amino}-3-cyano-6-{2-(cyclopropyl-methoxy)-6-[(4-methoxy-benzyl)oxy]phenyl}-4-pyridinyl)-1-piperidinecarboxylate as a brown solid (0.543 g, yield; 89%).

Workup

  1. temperatureAfter cooled to room temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with hexane and isopropyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-3439d006dfa14289b33c670ec79c216d
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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