Water → HCID 56592601, compound

HRID 1616092Notes

Reaction equation

HRID 1616092 reaction equation
C(=O)([O-])[O-].[K+].[K+].N1([O:16][C:17]2[C:18]3[O:25][CH:24]=[C:23]([CH:26]4[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]4)[C:19]=3[N:20]=[CH:21][N:22]=2)C2C=CC=CC=2N=N1.[N:39]1([C:44]2[CH:49]=[CH:48][C:47](O)=[CH:46][CH:45]=2)[CH:43]=[N:42][N:41]=[N:40]1.O>CN(C=O)C>[N:39]1([C:44]2[CH:49]=[CH:48][C:47]([O:16][C:17]3[C:18]4[O:25][CH:24]=[C:23]([CH:26]5[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:28][CH2:27]5)[C:19]=4[N:20]=[CH:21][N:22]=3)=[CH:46][CH:45]=2)[CH:43]=[N:42][N:41]=[N:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5429104-(1H-1,2,3,4-tetrazol-1-yl)phenolHCID 86681871HCID 86681871, compound

Product 1

HCID 56592601HCID 56592601, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (5.0 mg, 0.035 mmol) was added to a solution of the tert-butyl 4-{4-[(1H-benzo[d][1,2,3]triazol-1-yl)oxy]furo[3,2-d]pyrimidin-7-yl}piperidine-1-carboxylate obtained in Step 7 of Example 1 (10.0 mg, 0.023 mmol) and 4-(1H-tetrazol-1-yl)phenol (4.0 mg, 0.025 mmol) in DMF (0.2 mL), followed by stirring at 70° C. for 5 hours. Water was added to the reaction liquid, and the reaction liquid was extracted with chloroform:methanol=5:1 and concentrated under a reduced pressure. The obtained residue was purified by using silica gel chromatography (chloroform:methanol=50:1) to give the titled compound (7.4 mg, 70%) as a white solid.

Workup

  1. customthe reaction liquid
  2. extractionwas extracted with chloroform
  3. concentrationmethanol=5:1 and concentrated under a reduced pressure
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-19f4a3d92a3840db8877245e6225e6fb
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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