Triethylamine → (E)-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}-4-(morpholinocarbonylamino)piperidine

HRID 2075454Notes

Reaction equation

HRID 2075454 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:26]=[CH:25][C:15]([C:16]([N:18]3[CH2:23][CH2:22][CH:21]([NH2:24])[CH2:20][CH2:19]3)=[O:17])=[CH:14][CH:13]=2)=[N:2]1.C(N(CC)CC)C.[N:34]1([C:40](Cl)=[O:41])[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([N:18]3[CH2:19][CH2:20][CH:21]([NH:24][C:40]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[O:41])[CH2:22][CH2:23]3)=[O:17])=[CH:25][CH:26]=2)=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11221716(E)-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}-4-aminopiperidine

Product 1

HCID 67089582(E)-1-{4-[2-(1H-indazol-3-yl)vinyl]benzoyl}-4-(morpholinocarbonylamino)piperidineYield 0.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 64 (500 mg, 1.19 mmol) was dissolved in dichloromethane, and the solution was added with triethylamine (0.498 mL, 3.57 mmol), 4-morpholinecarbonyl chloride (468 mg, 2.62 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (200.2 mg, 1.04 mmol) at 0° C., followed by stirring for 4 hours to obtain Compound 99 (1.5 mg, 0.3%).

Sources & evidence

ORD record
ord-6e217ae951da4945bacf63aaa6728043
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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