4-Methylmorpholine → HCID 67549862, compound

HRID 43940Notes

Reaction equation

HRID 43940 reaction equation
[NH2:1][CH:2]1[CH2:10][CH2:9][C:8]2[C:4](=[CH:5][N:6]([C:11]3[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=3)[N:7]=2)[CH2:3]1.[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]([NH:1][CH:2]2[CH2:10][CH2:9][C:8]3[C:4](=[CH:5][N:6]([C:11]4[S:12][C:13]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:14]([CH3:16])[N:15]=4)[N:7]=3)[CH2:3]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 67549482HCID 67549482, compound

Product 1

HCID 67549862HCID 67549862, compoundYield 76%

Procedure

The same operation as in Example (217c) was performed using ethyl 2-(5-amino-4,5,6,7-tetrahydro-2H-indazol-2-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (243a) (127 mg, 0.42 mmol), 4-chloro-5-ethyl-1H-imidazole-2-carboxylic acid obtained in Example (1d) (72 mg, 0.42 mmol), WSC hydrochloride (239 mg, 1.25 mmol), 1-hydroxybenzotriazole (56 mg, 0.42 mmol) and N-methylmorpholine (0.09 mL, 0.83 mmol), to obtain 146 mg of the title compound as a pale yellow solid (76%).

Sources & evidence

ORD record
ord-f08a9b0ef7544edb9be503688a0174e3
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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