1,1'-Carbonyldiimidazole → HCID 10460949, compound

HRID 1492771Notes

Reaction equation

HRID 1492771 reaction equation
[C:1](N1C=CN=C1)([N:3]1C=CN=C1)=O.[Br:13][C:14]1[C:18]2[CH:19]=[C:20]([CH2:23][N:24]3[C:28]([C:29]([OH:31])=O)=[C:27]([CH3:32])[N:26]=[C:25]3[CH3:33])[CH:21]=[CH:22][C:17]=2[O:16][C:15]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[NH:40][S:41]([C:44]([F:47])([F:46])[F:45])(=[O:43])=[O:42]>C1COCC1>[Br:13][C:14]1[C:18]2[CH:19]=[C:20]([CH2:23][N:24]3[C:28]([C:29]([NH:3][CH3:1])=[O:31])=[C:27]([CH3:32])[N:26]=[C:25]3[CH3:33])[CH:21]=[CH:22][C:17]=2[O:16][C:15]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[NH:40][S:41]([C:44]([F:46])([F:45])[F:47])(=[O:42])=[O:43]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 10460693HCID 10460693, compound

Product 1

HCID 10460949HCID 10460949, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (0.17 g) was added to a solution of the product of Example 101 (0.2 g) in dry THF (15 ml) under a nitrogen atmosphere. The resulting solution was stirred at room temperature for 4 h, concentrated in vacuo to ~5 ml and then poured into an autoclave with 20 ml of liquid methylamine. The autoclave was heated to 60° C. for 1.5 h and then cooled to -40° C. before opening. The solution was diluted with cold methanol (-35° C.; 50 ml). The resulting solution was concentrated in vacuo and the residue was purified by flash chromatography eluting with chloroform-methanol (10:3) followed by another column eluted with 10-20% methanol in ethyl acetate to give the title compound as a white solid (104 mg), m.p. 208°-210° C.

Workup

  1. concentrationconcentrated in vacuo to ~5 ml
  2. additionpoured into an autoclave with 20 ml of liquid methylamine
  3. temperatureThe autoclave was heated to 60° C. for 1.5 h
  4. temperaturecooled to -40° C. before opening
  5. additionThe solution was diluted with cold methanol (-35° C.; 50 ml)
  6. concentrationThe resulting solution was concentrated in vacuo
  7. customthe residue was purified by flash chromatography
  8. washeluting with chloroform-methanol (10:3)
  9. washeluted with 10-20% methanol in ethyl acetate

Sources & evidence

ORD record
ord-65b8418f782743e3b91cc39e7bcc02c8
Source dataset
uspto-grants-1994_12
Patent number
US05374646

Reaction notes

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