2,4,6-Trimethylpyridine → HCID 131723240, compound

HRID 1937827Notes

Reaction equation

HRID 1937827 reaction equation
[CH2:1]([N:8]([CH3:34])[C:9]([CH:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=1)[C:12]([NH:14][C@@H:15]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:16](O)=[O:17])=[O:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC(C)=CC=1C.[NH2:68][CH2:69][CH:70]1[CH2:75][CH2:74][CH:73]([C:76]#[N:77])[CH2:72][CH2:71]1>CN(C)C=O>[CH2:1]([N:8]([CH3:34])[C:9](=[O:10])[CH:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]#[N:33])=[CH:28][CH:27]=1)[C:12]([NH:14][C@H:15]([C:16](=[O:17])[NH:77][CH2:76][CH:73]1[CH2:74][CH2:75][CH:70]([C:69]#[N:68])[CH2:71][CH2:72]1)[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 291897(4-cyano-cyclohexylmethyl)-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 131723239HCID 131723239, compound

Product 1

HCID 131723240HCID 131723240, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To [2-(R,S)-(Benzyl-methyl-carbamoyl)-3-(4-cyano-phenyl)-propionylamino]-(S)-cyclohexyl-acetic acid (910 mg, 1.97 mmol) in dimethylformamide (150 ml) were added HATU (825 mg, 2.17 mmol) and collidine (263 mg, 2.17 mmol) at 0° C. After 30 minutes at 0° C. 4-aminomethyl-cyclohexanecarbonitrile (272 mg, 1.97 mmol) was added. The mixture was stirred for 1 hour, then allowed to warm to room temperature, and stand at room temperature for 72 hours. After evaporation the residue was stirred with Na2CO3 solution and the precipitate was sucked off to yield 1.18 g of the desired product which was used for further reactions without purification.

Workup

  1. waitstand at room temperature for 72 hours
  2. customAfter evaporation the residue
  3. stirringwas stirred with Na2CO3 solution

Sources & evidence

ORD record
ord-ff78bf99d4ca4bbb986babe64c00a643
Source dataset
uspto-grants-2002_05
Patent number
US06395737B1

Reaction notes

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