Stannous chloride dihydrate → HCID 86647005, compound

HRID 1942991Notes

Reaction equation

HRID 1942991 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([NH:8][C:9]2[S:10][C:11]([CH3:23])=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=3)[N:13]=2)[CH:7]=1.O.O.Cl[Sn]Cl>CO>[NH2:20][C:16]1[CH:15]=[C:14]([C:12]2[N:13]=[C:9]([NH:8][C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:24][CH3:25])[S:10][C:11]=2[CH3:23])[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 25130140HCID 25130140, compound

Product 1

HCID 86647005HCID 86647005, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 12z (0.25 g, 0.66 mmol) and SnCl2.2H2O (1.35 g, 6.0 mmol) in methanol was refluxed for 48 h. Evaporation of the solvent under reduced pressure afforded 4-(3aminophenyl)-N-(5-chloro-2-methoxyphenyl)-5-methylthiazol-2-amine as a solid which was dissolved in chloroform and cooled in an ice bath to 0° C. Triethylamine (93 μL, 0.66 mmol) was added and the mixture was stirred for 15 min at the same temperature. Pivaloyl chloride (0.08 g, 0.66 mmol) was then added dropwise at 0° C. and the mixture was stirred overnight at which point the mixture was poured onto ice-cold water and the aqueous layer was extracted with DCM. The collected organic extract was washed with sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, and filtered. Evaporation of the solvent under reduced pressure afforded 13z as a yellowish white solid (0.21 g, 75%). Mp decomposition at 195° C. 1H NMR (300 MHz, CDCl3): δ 7.83 (s, 1H), 7.76 (s, 1H), 7.45 (m, 1H), 7.38 (d, J=2.40 Hz, 1H), 7.33 (s, 1H), 7.27 (m, 1H), 6.93 (d, J=9.0 Hz, 1H), 3.89 (s, 3H), 2.42 (s, 3H), 1.33 (s, 9H). 13C NMR (150 MHz, CDCl3): δ 177.4, 168.4, 151.5, 139.1, 129.9, 127.8, 125.9, 124.3, 123.6, 121.3, 120.3, 118.5, 114.5, 113.3, 111.4, 111.0, 56.4, 39.9, 27.7, 12.5. HRMS m/z (ESI) calcd. for C22H24ClN3O2S (M+H)+ 430.1351. Found 430.1345.

Workup

  1. temperaturewas refluxed for 48 h
  2. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0d241c1adf59447a97c7efb743f0d97e
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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