4-Methylmorpholine → N-(2-aminoethyl)acetamide

HRID 2075441Notes

Reaction equation

HRID 2075441 reaction equation
[ClH:1].[C:2]([NH:5][CH2:6][CH2:7][NH:8][C:9](=O)[C:10]1C=CC=[C:12](/[CH:16]=[CH:17]/[C:18]2C3C(=CC=CC=3)[NH:20][N:19]=2)C=1)(=[O:4])[CH3:3].[NH:28]1[C:36]2C(=CC=CC=2)C(/C=C/C2C=C(C=CC=2)C(O)=[O:43])=N1.[CH3:48][N:49]1[CH2:54][CH2:53]OC[CH2:50]1>>[C:2]([NH:5][CH2:6][CH2:7][NH2:8])(=[O:4])[CH3:3].[OH2:43].[OH:43][N:19]1[C:18]2[CH:17]=[CH:16][CH:12]=[CH:53][C:54]=2[N:49]=[N:20]1.[ClH:1].[CH2:9]([N:8]=[C:7]=[N:28][CH2:36][CH2:53][CH2:54][N:49]([CH3:48])[CH3:50])[CH3:10]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 67089624HCID 67089624, compoundHCID 67090547HCID 67090547, compound

Product 3

HCID 66082N-(2-aminoethyl)acetamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Procedure

In a similar manner to Example 5, Compound 38 (240 mg, 36%) was obtained using (E)-3-[2-(1H-indazol-3-yl)vinyl]benzoic acid (500 mg, 1.89 mmol) obtained in a similar manner to Step 6 of Example 1, N-acetylethylenediamine (290 mg, 3.82 mmol), 1-hydroxybenzotriazole monohydrate (332 mg, 2.46 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (510 mg, 2.66 mmol) and N-methylmorpholine (420 μL, 3.82 μmmol).

Sources & evidence

ORD record
ord-daa29b581d414a09b933c13972006e8b
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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