Stannous chloride dihydrate → HCID 86704004, compound

HRID 1773920Notes

Reaction equation

HRID 1773920 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=4)[C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:13]3)[CH2:4][CH2:3]1.O.O.[Sn](Cl)Cl>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:23]4[CH:24]=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=4)[C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:13]3)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 86704005HCID 86704005, compound

Product 1

HCID 86704004HCID 86704004, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(1-methylpiperidin-4-yloxy)-8-(3-nitrophenyl)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 242 B) (0.6 mmole), tin(II) chloride dihydrate (2.83 g) in ethanol (15 mL) is refluxed for 2 hours. The mixture is then cooled to room temperature and extracted twice with chloroform. Pooled organic extracts are dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC-MS (Waters AutoPurification HPLC/MS System, Sunfire Prep C18 5 μm OBD 30×150 mm column, eluents: water/0.1% formic acid (A) and acetonitrile/0.1% formic acid (B), focus gradient from 14% (B) to 24% (B) in 10 minutes) to afford 3-[4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-8-yl]-phenylamine melting at 120° C.

Workup

  1. temperatureis refluxed for 2 hours
  2. extractionextracted twice with chloroform
  3. dry with materialPooled organic extracts are dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by preparative HPLC-MS (Waters AutoPurification HPLC/MS System, Sunfire Prep C18 5 μm OBD 30×150 mm column, eluents: water/0.1% formic acid (A) and acetonitrile/0.1% formic acid (B), focus gradient from 14% (B) to 24% (B) in 10 minutes)

Sources & evidence

ORD record
ord-62121426afdd42809c89b2a897ea9f22
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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