Allyl chloroformate → HCID 86732422, compound

HRID 1776394Notes

Reaction equation

HRID 1776394 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH:25][C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:10]=2)=[N:7][CH:8]=1.[C:32](Cl)(=[O:37])[O:33][CH2:34][CH:35]=[CH2:36]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([N:25]([C:32]([O:33][CH2:34][CH:35]=[CH2:36])=[O:37])[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[N:5][C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[N:10]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 18052Allyl chloroformate2×HCID 86732421HCID 86732421, compound

Product 1

HCID 86732422HCID 86732422, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

96.3 mg of tert-butyl 3-[5-methoxy-4-(pyridin-4-ylamino)pyrimidin-2-yl]-1H-indazole-1-carboxylate (1-8-1, 0.23 mmol, 1 eq.) was suspended in 7 ml of pyridine. 27.7 mg of prop-2-en-1-yl carbonochloridate (0.23 mmol, 1 eq.) were added and stirred for two hours at room temperature. Twice 27.7 mg of prop-2-en-1-yl carbonochloridate (0.23 mmol, 1 eq.) were added again and stirred the first time for 24 hours and the second time for three days at room temperature. The reaction mixture was concentrated in vacuo. To the residue was added water and acidified with 1M aq. hydrogen chloride solution. This aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over a silicone filter and concentrated under vacuo. Purification by flash chromatography (ethyl acetate/methanol 0-50%) provided 50.8 mg (0.09 mmol, 39.97%) of the analytically pure target compound.

Workup

  1. stirringstirred the first time for 24 hours
  2. waitthe second time for three days at room temperature
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionTo the residue was added water
  5. extractionThis aqueous layer was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over a silicone
  8. filtrationfilter
  9. concentrationconcentrated under vacuo
  10. customPurification by flash chromatography (ethyl acetate/methanol 0-50%)
  11. customprovided 50.8 mg (0.09 mmol, 39.97%) of the analytically pure target compound

Sources & evidence

ORD record
ord-c8b2b79ced654e1f8a45c86ef3faed87
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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