Stannous chloride dihydrate → 17-Cyclohexyl-18-[4-[2-(4 methanesulfonylpiperazin-1-yl)-5-amino-benzyloxy]phenyl]-1,4,11-triazatricyclo[11.5.2.016,19]icosa-7,13 (20),14,16(19),17-pentaene-3,12-dione

HRID 39042Notes

Reaction equation

HRID 39042 reaction equation
O.O.[Sn](Cl)Cl.[CH:6]1([C:12]2[C:13]3[CH:14]=[CH:15][C:16]4[C:17](=[O:60])[NH:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][CH2:24][NH:25][C:26](=[O:59])[CH2:27][N:28]([C:57]=3[CH:58]=4)[C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]3[CH:43]=[C:42]([N+:44]([O-])=O)[CH:41]=[CH:40][C:39]=3[N:47]3[CH2:52][CH2:51][N:50]([S:53]([CH3:56])(=[O:55])=[O:54])[CH2:49][CH2:48]3)=[CH:32][CH:31]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C1COCC1.C(O)C>[CH:6]1([C:12]2[C:13]3[CH:14]=[CH:15][C:16]4[C:17](=[O:60])[NH:18][CH2:19][CH2:20][CH:21]=[CH:22][CH2:23][CH2:24][NH:25][C:26](=[O:59])[CH2:27][N:28]([C:57]=3[CH:58]=4)[C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]3[CH:43]=[C:42]([NH2:44])[CH:41]=[CH:40][C:39]=3[N:47]3[CH2:48][CH2:49][N:50]([S:53]([CH3:56])(=[O:54])=[O:55])[CH2:51][CH2:52]3)=[CH:32][CH:31]=2)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 74928751HCID 74928751, compound

Product 1

HCID 7492875217-Cyclohexyl-18-[4-[2-(4 methanesulfonylpiperazin-1-yl)-5-amino-benzyloxy]phenyl]-1,4,11-triazatricyclo[11.5.2.016,19]icosa-7,13 (20),14,16(19),17-pentaene-3,12-dione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Tin(II) chloride dihydrate (400 mg, 1.77 mmol) was added to a solution of 3 (55 mg, 0.0715 mmol) in THF (1 mL) and ethanol (1.5 mL). The reaction mixture was heated at reflux for 3 days, then allowed to cool down to room temperature. Then, volatiles were evaporated under vacuum and the residue was successively partitioned between a diluted solution of NaHCO3 and ethyl acetate, dried (Na2SO4) and evaporated. Purification by column chromatography (CH2Cl2/methanol, 97.5:2.5) afforded the title compound 4 as a yellowish powder: m/z=740 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 days
  3. customThen, volatiles were evaporated under vacuum
  4. customthe residue was successively partitioned between a diluted solution of NaHCO3 and ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customPurification by column chromatography (CH2Cl2/methanol, 97.5:2.5)

Sources & evidence

ORD record
ord-90ef2916b8e149bfbf3190a0132600ab
Source dataset
uspto-grants-2013_09
Patent number
US08524716B2

Reaction notes

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