4-Methylmorpholine → Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylate

HRID 43908Notes

Reaction equation

HRID 43908 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([N:14]2[CH2:17][CH:16]([NH:18][CH2:19][CH2:20][CH3:21])[CH2:15]2)[S:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])([CH3:3])[CH3:2].[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:16]2[CH2:17][N:14]([C:6]3[S:7][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:4]([CH:1]([CH3:3])[CH3:2])[N:5]=3)[CH2:15]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 675489294-chloro-5-ethyl-1H-imidazole-2-carboxylic acidHCID 68405794HCID 68405794, compound

Product 1

HCID 67549449Ethyl 2-(3-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl](n-propyl)amino}azetidin-1-yl)-4-isopropyl-1,3-thiazole-5-carboxylateYield 61.2%

Procedure

The same operation as in Example (221c) was performed using ethyl 4-isopropyl-2-[3-(n-propylamino)azetidin-1-yl]-1,3-thiazole-5-carboxylate obtained in Example (229b) (91 mg, 0.29 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (51 mg, 0.29 mmol), WSC hydrochloride (168 mg, 0.88 mmol), 1-hydroxybenzotriazole (39 mg, 0.29 mmol) and N-methylmorpholine (0.06 mL, 0.58 mmol), to obtain 83 mg of the title compound as a colorless oily substance (61%).

Sources & evidence

ORD record
ord-60f31edaed2a4f1b9474a709dd521eb0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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