2,4,6-Trimethylpyridine → HCID 54293223, compound

HRID 1883494Notes

Reaction equation

HRID 1883494 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH2:36])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC(C)=CC=1C>CN(C)C=O>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35][NH:36][C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 7368171-Boc-4-(aminomethyl)piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16218812(2S)-{[(Benzyloxy)carbonyl]amino}(cyclohexyl)acetic acid

Product 1

HCID 54293223HCID 54293223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (S)-benzyloxycarbonylamino-cyclohexyl-acetic acid (5.4 g, 18.66 mmol) and 4-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (4.0 g, 18.66 mmol) in dimethylformamide were added HATU (7.09 g, 18.66 mmol) and collidine (2.46 ml, 18.66 mmol) at 0° C. The mixture was stirred for 1 hour and then allowed to warm to room temperature. The mixture was evaporated and separated between ethyl acetate and sodium bicarbonate solution. The organic layer was washed with aqueous solution (pH 4), dried and evaporated. The resulting residue was taken up in ethyl acetate and washed with potassium hydrogen sulfate solution, dried and evaporated to give the desired product. Yield: 8.29 g (91%), MS m/z: 488.3 (M+H)+.

Workup

  1. customThe mixture was evaporated
  2. customseparated between ethyl acetate and sodium bicarbonate solution
  3. washThe organic layer was washed with aqueous solution (pH 4)
  4. customdried
  5. customevaporated
  6. washwashed with potassium hydrogen sulfate solution
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-4ef2fc6549b74c0a8e127b3eb45785f1
Source dataset
uspto-grants-2004_07
Patent number
US06759420B1

Reaction notes

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