Methanol → HCID 9895246, compound

HRID 1368629Notes

Reaction equation

HRID 1368629 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)=[C:15]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=3)(=[O:27])=[O:26])[N:14]([CH3:38])[N:13]=2)=[N:6][CH:7]=1.C[OH:40]>>[Br:1][C:2]1[CH:7]=[N:6][C:5]([O:8][CH2:9][CH2:10][O:11][C:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][OH:40])=[CH:19][CH:18]=3)=[C:15]([NH:24][S:25]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([CH3:35])([CH3:37])[CH3:36])=[CH:32][CH:33]=3)(=[O:26])=[O:27])[N:14]([CH3:38])[N:13]=2)=[N:4][CH:3]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 9894949N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

Product 1

HCID 9895246HCID 9895246, compound

Procedure

Streptomyces rimosus subsp. rimosus ATCC10970 maintained on a ¼ strength ATCC172 agar slope was inoculated as a loopful of spores into a 300 ml Erlenmeyer flask containing 50 ml of AS7-H inoculum medium. This was allowed to incubate for 2 days at 28° C., 200 rpm on an Infors Multitron™ Shaker with 1″ throw. 2 mls of this inoculum medium was then transferred to each of sixteen 300 ml Erlenmeyer flask containing 50 ml of AP-5H production medium and incubated under the same conditions for a further 24 hours. At this point 20 mg of N-[3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 3) dissolved in 0.5 ml of methanol was added to each of the flasks and the fermentation allowed to continue under the same conditions for a further 6 hours. Each flask was then extracted with 200 mls of ethyl acetate and the combined ethyl acetate solubles concentrated to dryness to give a gum solid, 1.4 g.

Workup

  1. temperaturerimosus ATCC10970 maintained on a ¼ strength ATCC172 agar slope
  2. additioncontaining 50 ml of AS7-H inoculum medium
  3. additioncontaining 50 ml of AP-5H production medium
  4. waitincubated under the same conditions for a further 24 hours
  5. additionwas added to each of the flasks
  6. waitto continue under the same conditions for a further 6 hours
  7. extractionEach flask was then extracted with 200 mls of ethyl acetate
  8. concentrationthe combined ethyl acetate solubles concentrated to dryness
  9. customto give a gum solid, 1.4 g

Sources & evidence

ORD record
ord-d71d7c18327442d590172089034a1648
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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