Hydrochloric Acid → HCID 178492691, compound

HRID 1005606Notes

Reaction equation

HRID 1005606 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:50]=[CH:49][CH:48]=[CH:47][C:14]=1[C:15]([NH:17][C:18]1[CH:44]=[CH:43][C:21]([C:22]([N:24]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=2[O:33][CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]#[N:42])=[CH:37][CH:36]=2)[CH3:25])=[O:23])=[CH:20][C:19]=1[O:45][CH3:46])=[O:16])=O)(C)(C)C.C[Sn]([N:55]=[N+:56]=[N-:57])(C)C.Cl.[Sn].N1C=NN=N1.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:50]=[CH:49][CH:48]=[CH:47][C:14]=1[C:15]([NH:17][C:18]1[CH:44]=[CH:43][C:21]([C:22]([N:24]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=2[O:33][CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]3[NH:42][N:57]=[N:56][N:55]=3)=[CH:39][CH:40]=2)[CH3:25])=[O:23])=[CH:20][C:19]=1[O:45][CH3:46])=[O:16]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 5352426Tin atomHCID 18791319HCID 18791319, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 178492691HCID 178492691, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-[2-[3-(tert-butoxycarbonyl)aminoprop-1-yl]oxybenzoyl]amino-3-methoxy-N-[2-(4-cyanophenylmethyl)oxy-4-methylphenyl]-N-methylbenzamide (360 mg) in xylene (8 ml) was added trimethyltin azide (218 mg) and the solution was stirred at 120° C. for 3 days. The solution was cooled to ambient temperature and 12N hydrochloric acid (10 ml) was added to the solution to decompose tin salt of the tetrazole compound and the excess reagent. Then the solution was adjusted to pH 7 with saturated aqueous sodium hydroxide at 0° C., and the solution was extracted with ethyl acetate (50 ml×3). The organic layer was washed with brine, and dried over magnesium sulfate. The solvent was evaporated to give a crude product. The crude product was purified by silica gel column chromatography (SiO2 30 g, 2-25% methanol in chloroform) to give 4-[2-(3-aminoprop-1-yl)oxybenzoyl]amino-3-methoxy-N-[2-[4-(tetrazol-5-yl)phenylmethyl]oxy-4-methylphenyl]-N-methylbenzamide (227 mg).

Workup

  1. temperatureThe solution was cooled to ambient temperature
  2. extractionthe solution was extracted with ethyl acetate (50 ml×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated
  6. customto give a crude product
  7. customThe crude product was purified by silica gel column chromatography (SiO2 30 g, 2-25% methanol in chloroform)

Sources & evidence

ORD record
ord-0d58a1e45a73471489b0d7c7306f29d5
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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