Diisopropylethylamine → HCID 90017038, compound

HRID 1055003Notes

Reaction equation

HRID 1055003 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][C:9]([OH:11])=O)=[N:5][C:4]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH2:50]([C:52]1[C:53]([NH:59][NH2:60])=[N:54][C:55]([CH3:58])=[N:56][CH:57]=1)[CH3:51]>CN(C)C=O>[CH2:50]([C:52]1[C:53]([NH:59][NH:60][C:9](=[O:11])[CH2:8][CH2:7][C:6]2[N:2]([CH3:1])[N:3]=[C:4]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[N:5]=2)=[N:54][C:55]([CH3:58])=[N:56][CH:57]=1)[CH3:51]

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 83891736HCID 83891736, compoundHCID 90016952HCID 90016952, compound

Product 1

HCID 90017038HCID 90017038, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Methyl-3-(pyrrolidin-1-yl)-1H-1,2,4-triazol-5-yl)propanoic acid (140 mg, 0.624 mmol), HATU (712 mg, 1.87 mmol) and N,N-diisopropylethylamine (600 μl, 3.53 mmol) were dissolved in dimethylformamide (18 mL). The mixture was stirred for 20 minutes. 5-Ethyl-4-hydrazinyl-2-methylpyrimidine (99 mg, 0.655 mmol) was added and the reaction mixture was allowed to stir at room temperature overnight. The mixture was concentrated to an oil. Preparative HPLC afforded the desired product (71 mg, 31%) as a yellow gum. MS: m/z=359.23 (M+H+)

Workup

  1. stirringto stir at room temperature overnight
  2. concentrationThe mixture was concentrated to an oil

Sources & evidence

ORD record
ord-d44a75693d2d43e09f9ea0eda6a18c1d
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

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