4-Methylmorpholine → HCID 67548590, compound

HRID 43910Notes

Reaction equation

HRID 43910 reaction equation
[CH2:1]([NH:5][CH:6]1[CH2:9][N:8]([C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4].[Cl:21][C:22]1[N:23]=[C:24]([C:29](O)=[O:30])[NH:25][C:26]=1[CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[CH2:1]([N:5]([C:29]([C:24]1[NH:25][C:26]([CH2:27][CH3:28])=[C:22]([Cl:21])[N:23]=1)=[O:30])[CH:6]1[CH2:9][N:8]([C:10]2[S:11][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:13]([CH3:15])[N:14]=2)[CH2:7]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 67549297HCID 67549297, compound

Product 1

HCID 67548590HCID 67548590, compoundYield 79.4%

Procedure

The same operation as in Example (221c) was performed using ethyl 2-[3-(n-butylamino)azetidin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (230c) (98 mg, 0.33 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (58 mg, 0.33 mmol), WSC hydrochloride (190 mg, 0.99 mmol), 1-hydroxybenzotriazole (46 mg, 0.33 mmol) and N-methylmorpholine (0.07 mL, 0.66 mmol), to obtain 119 mg of the title compound as a white solid (79%).

Sources & evidence

ORD record
ord-eb61d637779e4dd8abd3dfa2d05c7e90
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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