4-Methylmorpholine → HCID 178496038, compound

HRID 917564Notes

Reaction equation

HRID 917564 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[C:27]([CH2:29][OH:30])[CH:28]=1)[CH2:5][NH:6][C:7]([NH2:25])=[N:8][C:9]([C:11]1[C:12]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[N:13][S:14][C:15]=1[CH3:16])=[O:10].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:33].[CH3:44][N:45]1C[CH2:49][O:48][CH2:47][CH2:46]1.COCCN>C(Cl)Cl>[CH3:49][O:48][CH2:47][CH2:46][NH:45][C:44](=[O:33])[O:30][CH2:29][C:27]1[CH:26]=[C:4]([CH2:5][NH:6][C:7]([NH2:25])=[N:8][C:9]([C:11]2[C:12]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)=[N:13][S:14][C:15]=2[CH3:16])=[O:10])[CH:3]=[C:2]([Cl:1])[CH:28]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 80182-MethoxyethylamineHCID 821294-Nitrophenyl chloroformateHCID 178489178HCID 178489178, compound

Product 1

HCID 178496038HCID 178496038, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-((3-chloro-5-(hydroxymethyl)benzylamino)(amino)methylene)-3-(4-methoxyphenyl)-5-methylisothiazole-4carboxamide (Example 251) (20 mg) was treated with 4-nitrophenyl chloroformate (45 mg) and N-methyl morpholine (100 mg) in CH2Cl2 overnight, then 2-methoxyethanamine (30 mg) was added and stirring continued for 1.5 hours. The title compound was obtained as a white solid after HPLC purification.

Sources & evidence

ORD record
ord-3516b171696d46a0a1dd52452b7fc9c3
Source dataset
uspto-grants-2007_09
Patent number
US07273882B2

Reaction notes

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