4-Methylmorpholine → HCID 67548982, compound

HRID 43937Notes

Reaction equation

HRID 43937 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH2:19][CH2:20][CH3:21])[CH2:14][CH2:13]2)[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:22][C:23]1[N:24]=[C:25]([C:30](O)=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:22][C:23]1[N:24]=[C:25]([C:30]([N:18]([CH2:19][CH2:20][CH3:21])[CH:15]2[CH2:14][CH2:13][N:12]([C:4]3[S:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([CH3:1])[N:3]=3)[CH2:17][CH2:16]2)=[O:31])[NH:26][C:27]=1[CH2:28][CH3:29]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67548912Ethyl 4-methyl-2-[4-(n-propylamino)piperidin-1-yl]-1,3-thiazole-5-carboxylateHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acid

Product 1

HCID 67548982HCID 67548982, compoundYield 22.3%

Procedure

The same operation as in Example (221c) was performed using ethyl 4-methyl-2-[4-(n-propylamino)piperidin-1-yl]-1,3-thiazole-5-carboxylate obtained in Example (241d) (206 mg, 0.66 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (115 mg, 0.66 mmol), WSC hydrochloride (380 mg, 1.98 mmol), 1-hydroxybenzotriazole (89 mg, 0.66 mmol) and N-methylmorpholine (0.15 mL, 1.32 mmol), to obtain 69 mg of the title compound as a white solid (22%).

Sources & evidence

ORD record
ord-159a4622132047fdb031cd3fa34521e3
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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