Triethylamine → N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamide

HRID 2074121

Reaction equation

HRID 2074121 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][C:7]2[N:11]([CH2:12][C:13]([OH:15])=O)[N:10]=[C:9]([C:16]3[N:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH:20]=3)[CH:8]=2)=[CH:4][CH:3]=1.[CH3:32][C:33]([NH2:42])([CH3:41])[CH2:34][N:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:41][C:33]([NH:42][C:13](=[O:15])[CH2:12][N:11]1[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:31][CH:30]=2)=[CH:8][C:9]([C:16]2[N:17]=[N:18][N:19]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[CH:20]=2)=[N:10]1)([CH3:32])[CH2:34][N:35]1[CH2:36][CH2:37][O:38][CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2014972-Methyl-1-(morpholin-4-yl)propan-2-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67092066{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetic acid

Product 1

HCID 67091944N-(1,1-dimethyl-2-morpholin-4-ylethyl)-2-{5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetamideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {5-(4-fluorobenzyl)-3-[1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl]-1H-pyrazol-1-yl}acetic acid (1.0 g, 2.37 mmol), 1,1-dimethyl-2-morpholin-4-yl-ethylamine (0.375 g, 2.37 mmol), HATU (0.71 g, 2.85 mmol) and Et3N (0.71 g, 7.1 mol) in DMF (20 mL) was stirred at room temperature overnight. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and CH2Cl2 (50 mL). The aqueous layer was extracted with CH2Cl2 (2×20 mL). The combined organics were dried over Na2SO4 and evaporated to afford crude title compound (1.3 g, 92%) as yellow oil that was used without further purification in next step.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthe residue was treated with water (50 mL) and CH2Cl2 (50 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-c10ded2ac5914199a5d6b33f2d6c83ee
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Linked notes

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