1,2-Dichloroethane → 1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 410941Notes

Reaction equation

HRID 410941 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH3:12])=[C:6]([NH2:13])[CH:5]=1.[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:31]=[CH:30][C:25]3[N:26]=[C:27]([NH2:29])[S:28][C:24]=3[CH:23]=2)[CH:16]=1.[C:32](N1C=CN=C1)(N1C=CN=C1)=S.C(Cl)CCl>CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]([CH2:11][CH3:12])[C:32]([NH:29][C:27]3[S:28][C:24]4[CH:23]=[C:22]([O:21][C:17]5[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=5)[CH:31]=[CH:30][C:25]=4[N:26]=3)=[N:13][C:6]=2[CH:5]=1)=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 802641,1'-ThiocarbonyldiimidazoleHCID 12758354Methyl 3-amino-4-(ethylamino)benzoateHCID 866568766-(Pyridin-3-yloxy)-benzothiazol-2-ylamine

Product 1

HCID 866568751-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid methyl esterYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Ethyl-2-[6-(pyridin-3-yloxy)-benzothiazol-2-ylamino]-1H-benzoimidazole-5-carboxylic acid methyl ester (155.0 mg) was prepared by following General Procedure D starting from 3-amino-4-ethylamino-benzoic acid methyl ester (160.0 mg), 6-(pyridin-3-yloxy)-benzothiazol-2-ylamine (200.0 mg), 1,1′-thiocarbonyldiimidazole (200.0 mg), and EDC (200.0 mg) in DMF (2.0 mL).

Sources & evidence

ORD record
ord-fb74c3f1676245998084836a4d30d8d3
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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