Sodium Hydroxide → HCID 178450080, compound

HRID 1368554Notes

Reaction equation

HRID 1368554 reaction equation
C1(C(=[N:14][C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([C:25]([C:30]2[N:31]=[CH:32][N:33](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:34]=2)([OH:29])[CH:26]([CH3:28])[CH3:27])[CH:19]=[CH:18]3)C2C=CC=CC=2)C=CC=CC=1.NC1C=C2C(=CC=1)C=C(C(C1N=CN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)C=1)(O)C(C)C)C=C2.[CH3:94][S:95](Cl)(=[O:97])=[O:96].[OH-].[Na+]>ClCCl.N1C=CC=CC=1>[OH:29][C:25]([C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([NH:14][S:95]([CH3:94])(=[O:97])=[O:96])[CH:24]=[CH:23]2)([C:30]1[N:31]=[CH:32][NH:33][CH:34]=1)[CH:26]([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 22018326HCID 22018326, compoundHCID 22018411HCID 22018411, compound

Product 1

HCID 178450080HCID 178450080, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a similar manner to that described in Example 51-(ii), a reaction was carried out by using 1-{6-[(diphenylmethylene)amino]naphthalen-2-yl}-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (2.0 g) to give crude product containing 1-(6-aminonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol as a pale yellow oily substance. The crude product was dissolved in dichloromethane (10 ml). To the solution were added pyridine (0.71 ml) and methanesulfonyl chloride (0.34 ml) under ice cooling, and the mixture was stirred for 30 min. To the mixture was added 0.1N-aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent, hexane:ethyl acetate=1:1) to give the titled compound (1.16 g) as a pale yellow powder.

Workup

  1. customto give crude product
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fef7cdf58c1d49308e8f0e18adb93ee2
Source dataset
uspto-grants-2003_06
Patent number
US06573289B1

Reaction notes

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