Hydrochloric Acid → (1R,2R)-2-methyl-cyclopropanecarboxylic acid [3-(2-methyl-2H-indazol-5-yl)-4-pyridin-2-yl-isothiazol-5-yl]-amide hydrochloride

HRID 2079757Notes

Reaction equation

HRID 2079757 reaction equation
Br[C:2]1[N:7]=[C:6](N(C)C)[CH:5]=[CH:4][CH:3]=1.Br[C:12]1[C:13]([C:24]2[CH:32]=[CH:31][C:30]3[C:26](=[CH:27][N:28]([CH2:33]C)[N:29]=3)[CH:25]=2)=[N:14][S:15][C:16]=1[NH:17][C:18]([C@@H:20]1[CH2:22][C@H:21]1[CH3:23])=[O:19].BrC1C(C2C=CC3C(=CN(C)N=3)C=2)=NSC=1NC([C@@H]1C[C@H]1C)=O.[ClH:58]>>[ClH:58].[CH3:33][N:28]1[CH:27]=[C:26]2[C:30]([CH:31]=[CH:32][C:24]([C:13]3[C:12]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:7]=4)=[C:16]([NH:17][C:18]([C@@H:20]4[CH2:22][C@H:21]4[CH3:23])=[O:19])[S:15][N:14]=3)=[CH:25]2)=[N:29]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 140060626-bromo-N,N-dimethylpyridin-2-amineHCID 67103132(1R,2R)-2-methyl-cyclopropane carboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amideHCID 67103655(1R,2R)-2-methyl-cyclopropanecarboxylic acid [4-bromo-3-(2-ethyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide

Product 1

HCID 67103556(1R,2R)-2-methyl-cyclopropanecarboxylic acid [3-(2-methyl-2H-indazol-5-yl)-4-pyridin-2-yl-isothiazol-5-yl]-amide hydrochloride

Procedure

The following compounds are prepared essentially as described in Example 5 using (6-bromo-pyridin-2-yl)-dimethyl-amine and either (1R,2R)-2-methyl-cyclopropanecarboxylic acid [4-bromo-3-(2-ethyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide or (1R,2R)-2-methyl-cyclopropanecarboxylic acid [4-bromo-3-(2-methyl-2H-indazol-5-yl)-isothiazol-5-yl]-amide. Example 7; is prepared as the free base by omitting treatment with hydrogen chloride.

Workup

  1. customThe following compounds are prepared essentially
  2. customis prepared as the free base

Sources & evidence

ORD record
ord-17b82e23b7e7447a9ed64ca2b565f35e
Source dataset
uspto-grants-2011_04
Patent number
US07932274B2

Reaction notes

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