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Ammonium Chloride → (S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

HRID 1672832
Notes
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Reaction equation

HRID 1672832 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]3[N:19]=[C:20]([S:23][CH3:24])[N:21]=[CH:22][C:11]=3[C:10]2=[O:25])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Cl-].[NH4+].[N-:28]=[N+:29]=[N-:30].[Na+]>CN(C=O)C>[CH3:24][S:23][C:20]1[N:21]=[CH:22][C:11]2[C:10](=[O:25])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]4[N:28]=[N:29][NH:30][N:2]=4)[CH:4]=3)[CH2:18][C@H:17]3[N:13]([CH2:14][CH2:15][CH2:16]3)[C:12]=2[N:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67351154(S)-5-(3-Cyanophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one

Product 1

HCID 67350905(S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
100 °C

Procedure

(S)-5-(3-Cyanophenyl)-9-methylthio-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (366 mg, 1.04 mol) obtained in Step 1 of Example 71 was dissolved in DMF (7 mL), and the mixture was stirred at 100° C. for 9.5 hours after adding ammonium chloride (222 mg, 4.16 mmol) and sodium azide (176 mg, 2.71 mmol). The mixture was extracted by addition of ethyl acetate and water. The aqueous layer was collected, and the pH was adjusted to 5 with 1 mol/L hydrochloric acid. After extraction with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and reslurried with diethyl ether to give (S)-9-methylthio-5-[3-(2H-tetrazol-5-yl)phenyl]-1,2,3,3a,4,5-hexahydro-5,8,10,10b-tetraazabenzo[e]azulen-6-one (293 mg, 71%).

Workup

  1. extractionThe mixture was extracted by addition of ethyl acetate and water
  2. customThe aqueous layer was collected
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43d3bf11b0f149379f3743ec05536712
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07998954B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes