Pyrazinamide → Isoniazid

HRID 220338

Reaction equation

HRID 220338 reaction equation
[CH:1]1[C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=[N:3][CH:2]=1.CC1C2O[C@:19]3(C)OC=C[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)C=CC=[C:36](C)[C:37]([NH:39][C:40]4[C:43](/[CH:46]=N/N5CCN(C)CC5)=[C:44](O)[C:15]([C:16]=2[C:20]3=O)=[C:14]([C:41]=4O)C=1O)=O.[CH3:70][C@@H:71]1[O:75][C@@H:74]([O:76][C@H:77]2[C@H:82]([OH:83])[C@@H:81]([OH:84])[C@H:80]([NH:85][C:86]([NH2:88])=[NH:87])[C@@H:79]([OH:89])[C@@H:78]2[NH:90][C:91]([NH2:93])=[NH:92])[C@H:73]([O:94][C@@H:95]2[O:100][C@@H:99]([CH2:101][OH:102])[C@H:98]([OH:103])[C@@H:97]([OH:104])[C@@H:96]2[NH:105][CH3:106])[C@@:72]1([OH:109])[CH:107]=[O:108].[CH3:110][CH2:111][C@H:112]([NH:115][CH2:116][CH2:117][NH:118][C@H:119]([CH2:122][OH:123])[CH2:120][CH3:121])[CH2:113][OH:114].N1C=CN=CC=1C(N)=O>CO>[CH:1]1[C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=[N:3][CH:2]=1.[CH3:70][C@@H:71]1[O:75][C@@H:74]([O:76][C@H:77]2[C@H:82]([OH:83])[C@@H:81]([OH:84])[C@H:80]([NH:85][C:86]([NH2:88])=[NH:87])[C@@H:79]([OH:89])[C@@H:78]2[NH:90][C:91]([NH2:93])=[NH:92])[C@H:73]([O:94][C@@H:95]2[O:100][C@@H:99]([CH2:101][OH:102])[C@H:98]([OH:103])[C@@H:97]([OH:104])[C@@H:96]2[NH:105][CH3:106])[C@@:72]1([OH:109])[CH:107]=[O:108].[CH3:121][CH2:120][C@H:119]([NH:118][CH2:117][CH2:116][NH:115][C@H:112]([CH2:113][OH:114])[CH2:111][CH3:110])[CH2:122][OH:123].[CH3:73][C:72]([CH3:107])=[CH:71][CH2:4][CH2:5]/[C:6](/[CH3:7])=[CH:1]/[CH2:2][NH:3][CH2:36][CH2:37][NH:39][CH:40]1[CH:41]2[CH2:14][CH:15]3[CH2:16][CH:20]([CH2:19]2)[CH2:46][CH:43]1[CH2:44]3

Participants

10

Reactant 5

HCID 1046PyrazinamideHCID 3767IsoniazidHCID 14052EthambutolHCID 135398735RifampicinHCID 178484872HCID 178484872, compound

Product 4

HCID 3767IsoniazidHCID 14052EthambutolHCID 5274428N1-[(2E)-3,7-Dimethyl-2,6-octadien-1-yl]-N2-tricyclo[3.3.1.13,7]dec-2-yl-1,2-ethanediamineHCID 178484872HCID 178484872, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-80 °C

Procedure

Antimicrobial drugs isoniazid, rifampicin, streptomycin, and ethambutol were purchased from Sigma-Aldrich. St. Louis, Mo. Stock solutions of isoniazid, streptomycin, and ethambutol were prepared in distilled and deionized water at 10 mg/mL, sterilized by filtration, and stored frozen at −80° C. Stock solutions of rifampicin, at 1 or 10 mg/mL, were prepared in methanol and stored at −80° C. Pyrazinamide was purchased as the drug reconstituting kit from Becton Dickinson, Cockeysville, Md., and a stock solution was prepared following instructions by the manufacturer. Stock solutions of SQ109 were prepared in methanol at 1 mg/mL and stored at 80° C.

Workup

  1. distillationin distilled
  2. filtrationdeionized water at 10 mg/mL, sterilized by filtration
  3. customStock solutions of rifampicin, at 1 or 10 mg/mL, were prepared in methanol
  4. customstored at −80° C
  5. custom, and a stock solution was prepared
  6. customstored at 80° C.

Sources & evidence

ORD record
ord-7db65914d01d4f049bfc3bd1369acb02
Source dataset
uspto-grants-2012_06
Patent number
US08202910B2

Linked notes

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