Triethylamine → HCID 56593682, compound

HRID 601046Notes

Reaction equation

HRID 601046 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 isolated.

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-84f84eaa1a0c45b883ef2fbf2803ba16
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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