Methanesulfonic Acid → HCID 178477847, compound

HRID 1634580Notes

Reaction equation

HRID 1634580 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:30]2[CH:34]=[C:33]([CH:35]([CH2:38][CH2:39][CH2:40][CH3:41])C=O)[N:32]=[CH:31]2)C=CC=CC=1.[CH3:54]S(O)(=O)=O.S([O-])([O-])(=O)=O.[Mg+2].C([BH3-])#N.[Na+].O1CCCC1>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:17][CH2:18][N:19]([CH2:54][CH2:41][CH2:40][CH2:39][CH2:38][CH2:35][C:33]4[N:32]=[CH:31][NH:30][CH:34]=4)[CH2:20][CH2:21]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1

Participants

8

Reactant 6

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 24083Sulfuric acid magnesium salt (1:1)HCID 124087DesloratadineHCID 5003444Sodium cyanoborohydrideHCID 86585407HCID 86585407, compound

Product 1

HCID 178477847HCID 178477847, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (10) (284 mg; 0.914 mmol), (disclosed in published application WO 95/10516, Apr. 20, 1995), -[1-(triphenylmethyl)-1H-imidazol-4-yl]-hexanal (7) (393 mg; 0.962 mmol) and methanesulfonic acid (0.06 mL; 0.914 mmol)) in anhydrous methanol (10 mL), was added anhydrous magnesium sulfate (220 mg). The resultant suspension was stirred at room temperature for 30 min. A 1.0M solution of sodium cyanoborohydride in tetrahydrofuran (0.64 mL; 0.64 mmol) was added and the resultant mixture allowed to stir at room temperature for 23 h. The reaction mixture was filtered through Celite, and the filtrate evaporated under reduced pressure to obtain the mesylate salt of the imidazole-N-tritylated precursor of the title compound as a pink glass, which was detritylated without further purification. FABMS: 703 (MH+; 35%); 243 (Ph3C+; 100%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-44ae40c222694f77ab46fa0d94d5a350
Source dataset
uspto-grants-2003_01
Patent number
US06506756B2

Reaction notes

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