3-Aminopyridine → HCID 88719081, compound

HRID 1153937Notes

Reaction equation

HRID 1153937 reaction equation
C([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:59]/[O:60][CH3:61])/[C:27]([NH:29][CH:30]2[C:57](=[O:58])[N:32]3[C:33]([C:41]([O:43]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:42])=[C:34]([CH:37]=[CH:38][CH2:39]I)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2:62][C:63]1[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=1>C(Cl)Cl>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:59]/[O:60][CH3:61])/[C:27]([NH:29][CH:30]2[C:57](=[O:58])[N:32]3[C:33]([C:41]([O-:43])=[O:42])=[C:34](/[CH:37]=[CH:38]/[CH2:39][N+:65]4[CH:66]=[CH:67][CH:68]=[C:63]([NH2:62])[CH:64]=4)[CH2:35][S:36][C@H:31]23)=[O:28])[N:25]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 172930622HCID 172930622, compound

Product 1

HCID 88719081HCID 88719081, compoundYield 9.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diphenylmethyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(3-iodo-1-propen-1-yl)-3-cephem-4-carboxylate (X-1, 738 mg, 0.8 mmole) and 3-aminopyridine (113 mg, 1.2 mmole) in methylene chloride (15 ml) was stirred at room temperature for 1.5 hours and then concentrated under reduced pressure. The residue was triturated with diisopropyl ether and treated with a mixture of 90% trifluoroacetic acid (TFA) (8 ml) and anisole (1.6 ml) at room temperature for 1 hour, and then was concentrated and triturated with ether. The resulting crude product was purified by column chromatography using HP-20 (eluted with 10% methanol and 30% methanol) and the packing in a PrepPAK-500/C18 cartridge (Waters) (eluted with 5% methanol). The desired fraction was concentrated and lyophilized to give 38 mg (9%) of the title compound (I-1E). Estimated purity, 55%. M.p. >170° C. (dec.).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with diisopropyl ether
  3. additiontreated with a mixture of 90% trifluoroacetic acid (TFA) (8 ml) and anisole (1.6 ml) at room temperature for 1 hour
  4. concentrationwas concentrated
  5. customtriturated with ether
  6. customThe resulting crude product was purified by column chromatography
  7. washHP-20 (eluted with 10% methanol and 30% methanol)
  8. washthe packing in a PrepPAK-500/C18 cartridge (Waters) (eluted with 5% methanol)
  9. concentrationThe desired fraction was concentrated

Sources & evidence

ORD record
ord-51346f4a20ab4fcab0ac55f00c3f3e0b
Source dataset
uspto-grants-1984_12
Patent number
US04486586

Reaction notes

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