(1,3)Thiazolo(4,5-c)pyridin-2-amine → HCID 172930627, compound

HRID 1153935Notes

Reaction equation

HRID 1153935 reaction equation
C([O:5][C:6]([C:8]1([O:12]/[N:13]=[C:14](/[C:47]2[N:48]=[C:49]([NH:52]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:50][CH:51]=2)\[C:15]([NH:17][CH:18]2[C:45](=[O:46])[N:20]3[C:21]([C:29]([O:31]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:30])=[C:22]([CH:25]=[CH:26][CH2:27]I)[CH2:23][S:24][C@H:19]23)=[O:16])[CH2:11][CH2:10][CH2:9]1)=[O:7])(C)(C)C.[NH2:72][C:73]1[S:74][C:75]2[CH:80]=[CH:79][N:78]=[CH:77][C:76]=2[N:81]=1>CS(C)=O.C(OCC)(=O)C>[NH2:52][C:49]1[S:50][CH:51]=[C:47](/[C:14](=[N:13]/[O:12][C:8]2([C:6]([OH:7])=[O:5])[CH2:11][CH2:10][CH2:9]2)/[C:15]([NH:17][CH:18]2[C:45](=[O:46])[N:20]3[C:21]([C:29]([O-:31])=[O:30])=[C:22](/[CH:25]=[CH:26]/[CH2:27][N+:78]4[CH:79]=[CH:80][C:75]5[S:74][C:73]([NH2:72])=[N:81][C:76]=5[CH:77]=4)[CH2:23][S:24][C@H:19]23)=[O:16])[N:48]=1

Participants

5

Reactant 2

HCID 14252938(1,3)Thiazolo(4,5-c)pyridin-2-amineHCID 172930626HCID 172930626, compound

Product 1

HCID 172930627HCID 172930627, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(1-t-butoxycarbonylcyclobut-1-oxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-5', 641 mg, 0.58 mmole) and 2-aminothiazolo[4,5-c]pyridine (97 mg, 0.64 mmole) in dimethylsulfoxide (10 ml) was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate (150 ml), washed with water (2×150 ml), dried over sodium sulfate and concentrated under reduced pressure. The oily residue was triturated with diisopropyl ether and the resulting precipitate (558 mg) was treated with a mixture of 90% trifluoroacetic acid (10 ml) and anisole (2 ml) at room temperature for 1 hour. Concentration of the mixture followed by trituration of the residue with ether gave 313 mg of crude I-5C, which was purified by column chromatography [HP-20, eluted with 30% and 50% CH3OH: the packing in the PrepPAK-500/C18 (Waters), eluted with 10% CH3OH] to give 40 mg (11%) of I-5C. M.p. >150° C. (dec.).

Workup

  1. washwashed with water (2×150 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe oily residue was triturated with diisopropyl ether
  5. additionthe resulting precipitate (558 mg) was treated with a mixture of 90% trifluoroacetic acid (10 ml) and anisole (2 ml) at room temperature for 1 hour
  6. customgave 313 mg of crude I-5C, which
  7. customwas purified by column chromatography [HP-20
  8. washeluted with 30% and 50% CH3OH
  9. washthe packing in the PrepPAK-500/C18 (Waters), eluted with 10% CH3OH]
  10. customto give 40 mg (11%) of I-5C

Sources & evidence

ORD record
ord-6221543ab5ea4a9b9ffd7003680715b6
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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