Pyridine → HCID 73505443, compound

HRID 590857Notes

Reaction equation

HRID 590857 reaction equation
[NH2:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[N:4]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.N1C=CC=CC=1.Cl[C:49]([O:51][CH3:52])=[O:50]>C(Cl)Cl>[C:17]1([C@H:15]([NH:14][C:12](=[O:13])[NH:11][C:9]2[N:8]=[CH:7][C:6]3[C:2]([NH:1][C:49](=[O:50])[O:51][CH3:52])=[N:3][N:4]([C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:5]=3[CH:10]=2)[CH3:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformate2×HCID 118271680HCID 118271680, compound

Product 1

HCID 73505443HCID 73505443, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 50 mL round bottom flask charged with (R)-1-(3-amino-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (380 mg, 0.705 mmol) in DCM (10 ml) was added pyridine (1 ml) followed by methyl chloroformate (65 μl, 0.847 mmol). The flask was capped and the contents stirred at room temperature for 16 h. An additional aliquot of methyl chloroformate (65 μL, 0.847 mmol) was added to push the reaction to completion. The volatiles were removed in vacuo, the resulting residue redissolved in DCM and washed with saturated copper sulfate solution (2×10 mL). The organics were separated using a phase separator cartridge and concentrated. The resulting residue was purified by flash column chromatography on silica gel (ISCO; 80 g prepacked) eluting with ethyl acetate/hexanes to give (R)-methyl (6-(3-(1-phenylethyl)ureido)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-yl)carbamate (371 mg, 0.622 mmol, 88%) as a white solid. MS ESI calc'd. For C36H33N6O3 [M+H]+ 597. found 597.

Workup

  1. customThe flask was capped
  2. customthe reaction to completion
  3. customThe volatiles were removed in vacuo
  4. dissolutionthe resulting residue redissolved in DCM
  5. washwashed with saturated copper sulfate solution (2×10 mL)
  6. customThe organics were separated
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash column chromatography on silica gel (ISCO; 80 g prepacked)
  9. washeluting with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-93c2223577a244248d18434b096b189a
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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