Hydrochloric Acid → HCID 86639689, compound

HRID 1426148Notes

Reaction equation

HRID 1426148 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH3:27])[N:26]=2)=[N:11][CH:12]=[C:13](/[CH:15]=[CH:16]/[CH2:17][N:18]([CH3:20])[CH3:19])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1C=CC(S(NN)(=O)=O)=CC=1.[ClH:40]>>[ClH:40].[ClH:40].[CH2:1]([O:8][C:9]1[C:10]([NH:21][C:22]2[S:23][CH:24]=[C:25]([CH3:27])[N:26]=2)=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 15303P-ToluenesulfonylhydrazideHCID 16661155HCID 16661155, compound

Product 1

HCID 86639689HCID 86639689, compoundYield 31%

Procedure

(E)-3-(benzyloxy)-5-(3-(dimethylamino)prop-1-enyl)-N-(4-methylthiazol-2-yl)pyridin-2-amine (140 mg, 0.368 mmol) and 4-methylbenzenesulfonohydrazide (343 mg, 1.84 mmol) were reacted according to the method of Example 93 to afford the title compound (52 mg, 31.0% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) δ 11.05 (bs, 1H), 10.66 (bs, 1H), 7.87 (s, 1H), 7.62 (m, 3H), 7.45-7.32 (m, 3H), 6.83 (s, 1H), 5.34 (s, 2H), 2.98 (m, 2H), 2.71 (d, 6H), 2.66 (t, 2H), 2.31 (s, 3H), 2.01 (m, 2H). Mass spectrum (apci) m/z=383.2 (M+H-2HCl).

Sources & evidence

ORD record
ord-dfb4d25e4f234b4ba2c42f80c6fcb6ac
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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