1,2-Dichloroethane → HCID 178426307, compound

HRID 1163403Notes

Reaction equation

HRID 1163403 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[CH:16][C:15]=2[C:22](=[O:33])[NH:23][C:24]2[CH:32]=[C:31]3[C:27]([CH:28]=[N:29][NH:30]3)=[CH:26][CH:25]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[N:35]([C:38]1C=[CH:42][CH:41]=[CH:40][C:39]=1[C:44](F)(F)F)=[C:36]=S.C(Cl)CCl.C[N:53](C=O)C>>[C:1]([O:5][C:6](=[O:34])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([C:14]2[C:15]([C:22](=[O:33])[NH:23][C:24]3[CH:32]=[C:31]4[C:27]([CH:28]=[N:29][NH:30]4)=[CH:26][CH:25]=3)=[CH:16][C:17]3[N:21]=[C:36]([NH:35][C:38]4[C:39]([CH3:44])=[CH:40][CH:41]=[CH:42][N:53]=4)[NH:20][C:18]=3[CH:19]=2)[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 7371622-(Trifluoromethyl)phenyl isothiocyanateHCID 68445682HCID 68445682, compound

Product 1

HCID 178426307HCID 178426307, compound

Procedure

A solution of {1-[4,5-diamino-2-(1H-indazol-6-ylcarbamoyl)-phenyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (0.3 mmol; see Example 155) in DMF (1 mL) was reacted with 1-isothiocyanato-2-trifluoromethylbenzene (0.3 mmol) followed by cyclization in situ using EDC as described in general procedure B to provide {{1-[6-(1H-Indazol-6-ylcarbamoyl)-2-(3-methylpyridin-2-ylamino)-3H-benzoimidazol-5-yl]-piperidin-4-yl}-carbamic acid tert-butyl ester. MS: m/z 582 (M+H)+.

Sources & evidence

ORD record
ord-fa01021134014c038c39bc52a4a587af
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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