Triethylamine → HCID 56593682, compound

HRID 1179250Notes

Reaction equation

HRID 1179250 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([NH:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=2)[N:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[N:47]1([CH2:53][CH2:54][NH2:55])[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.C(N(CC)CC)C>O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[N:5]=[C:4]([NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([NH:55][CH2:54][CH2:53][N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[O:20])=[CH:21][CH:22]=2)[N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4082852-MorpholinoethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58976276HCID 58976276, compound

Product 1

HCID 56593682HCID 56593682, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(5-amino-1-pyridin-2-yl-1H-[1,2,4]triazol-3-ylamino)-benzoic acid (4.635 g, 15.643 mmole) in tetrahydrofuran (50 mL) was added (7.12 g, 1.2 equivalents) of HBTU, followed by 2-morpholin-4-yl-ethylamine (2.24 g, 1.1 equivalents) and triethylamine (5.45 mL, 2.5 equivalents). The reaction was stirred overnight at room temperature. The solid was filtered, washing with tetrahydrofuran, cold ethanol, water, ethanol, and finally ether. The compound was dried to provide 4-(5-amino-1-pyridin-2-yl-1H-[1,2,4]triazol-3-ylamino)-N-(2-morpholin-4-yl-ethyl)-benzamide (1.17 g, 18% yield) as a white solid. The organic phases contained product also but was not further islolated.

Workup

  1. filtrationThe solid was filtered
  2. washwashing with tetrahydrofuran, cold ethanol, water, ethanol, and finally ether
  3. customThe compound was dried

Sources & evidence

ORD record
ord-38136533e1c747d291c0997284bccd91
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Reaction notes

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