Diisopropylethylamine → [5-({[1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928415Notes

Reaction equation

HRID 928415 reaction equation
[OH:1][CH2:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([OH:15])=O)[N:10]=[N:9]2)=[CH:5][CH:4]=1.[C:18]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH2:32][NH2:33])=[C:27]([CH3:34])[N:26]=1)([CH3:21])([CH3:20])[CH3:19].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[C:18]([O:22][C:23](=[O:35])[NH:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([CH2:32][NH:33][C:13]([C:11]2[N:10]=[N:9][N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][OH:1])=[CH:17][CH:16]=3)[CH:12]=2)=[O:15])=[C:27]([CH3:34])[N:26]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22475372N-[5-(aminomethyl)-4,6-dimethyl(2-pyridyl)] (tert-butoxy)carboxamideHCID 580813181-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid

Product 1

HCID 58081262[5-({[1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(4-hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.95 g, 4.07 mmol), (5-Aminomethyl-4,6-dimethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (1.024 g, 4.07 mmol), HATU (2.013 g, 5.30 mmol) and DIPEA (2.85 mL, 16.29 mmol) in 50 mL DMF was stirred at room temperature for 3 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed with 1 n HCl solution and saturated sodium bicarbonate solution. The organic solution was dried over MgSO4, filtered and concentrated to yield the crude product which was used in the next step without further purification. LCMS (Method A) RtA=1.279; [M+H]+=467.0.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washwashed with 1 n HCl solution and saturated sodium bicarbonate solution
  3. dry with materialThe organic solution was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f61457ea26d4292830f4617b48fa8f6
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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