Morpholine → HCID 57799557, compound

HRID 2101059Notes

Reaction equation

HRID 2101059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([OH:15])=O)=[N:8][C:7]([NH:16][C:17]1[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=1)=[CH:6]2.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=[O:15])=[N:8][C:7]([NH:16][C:17]1[CH:21]=[C:20]([CH3:22])[NH:19][N:18]=1)=[CH:6]2

Participants

7

Reactant 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57799594HCID 57799594, compound

Product 1

HCID 57799557HCID 57799557, compoundYield 16.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 6-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinoline-1-carboxylic acid (100 mg) (example 9A), morpholine (70 mg), 1-hydroxybenzotriazole (HOBt) (130 mg), NMP (100 mg), N,N-dimethylformamide (DMF) (2 ml), 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride (EDCI) (180 mg) was stirred at room temperature overnight. The reaction mixture was purified by preparative LC-MS to give 20 mg of [6-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-yl]-morpholin-4-yl-methanone. LC-MS: m/e 368(MH+).

Workup

  1. customThe reaction mixture was purified by preparative LC-MS

Sources & evidence

ORD record
ord-d7b2f5c980c7419899dfbb321692bb71
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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