Hydrochloric Acid → HCID 86639691, compound

HRID 1426152Notes

Reaction equation

HRID 1426152 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[N:11][CH:12]=[C:13]([CH:15]=[CH:16][CH2:17][CH2:18][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:39]>>[ClH:39].[CH2:1]([O:8][C:9]1[C:10]([NH:20][C:21]2[S:22][CH:23]=[C:24]([CH3:26])[N:25]=2)=[N:11][CH:12]=[C:13]([CH2:15][CH2:16][CH2:17][CH2:18][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 72238000HCID 72238000, compound

Product 1

HCID 86639691HCID 86639691, compoundYield 37.7%

Procedure

N-(3-(benzyloxy)-5-(pent-1-enyl)pyridin-2-yl)-4-methylthiazol-2-amine (360 mg, 0.98 mmol) and 4-methylbenzenesulfonohydrazide (733 mg, 3.94 mmol) were reacted according to Example 93 to afford the title compound (150.2 mg, 37.7% yield) as a white solid after HCl salt formation. 1H NMR (DMSO-d6) 11.24 (bs, 1H), 7.83 (d, 1H), 7.61 (d, 2H), 7.56 (d, 2H), 7.44-7.32 (m, 3H), 6.87 (s, 1H), 5.34 (s, 2H), 2.57 (t, 2H), 2.33 (s, 3H), 1.57 (m, 2H), 1.35-1.18 (m, 4H), 0.85 (t, 3H). Mass spectrum (apci) m/z=368.1 (M+H-HCl).

Sources & evidence

ORD record
ord-ebe595673dd1404ebcb46fad71ca6598
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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