Methanol → HCID 46232721, compound

HRID 1093231Notes

Reaction equation

HRID 1093231 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]3[N:18]([CH:21]4[CH2:26][CH2:25]C(=O)[CH2:23][CH2:22]4)[N:19]=[CH:20][C:15]3=[C:14]([N:28]3[CH2:34][CH:33]4[O:35][CH:30]([CH2:31][CH2:32]4)[CH2:29]3)[N:13]=2)=[CH:8][CH:7]=1)=[O:4].CO[CH:38]([O:41][CH3:42])[O:39][CH3:40].CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH3:42][O:41][C:38]1([O:39][CH3:40])[CH2:25][CH2:26][CH:21]([N:18]2[C:16]3=[N:17][C:12]([C:9]4[CH:8]=[CH:7][C:6]([NH:5][C:3]([NH:2][CH3:1])=[O:4])=[CH:11][CH:10]=4)=[N:13][C:14]([N:28]4[CH2:34][CH:33]5[O:35][CH:30]([CH2:31][CH2:32]5)[CH2:29]4)=[C:15]3[CH:20]=[N:19]2)[CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 25260758HCID 25260758, compound

Product 1

HCID 46232721HCID 46232721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-3-{4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-(4-oxocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}urea (80 mg) (0.17 mmol) in DCM (2.0 mL) was added trimethylorthoformate and methanol in excess and a catalytic amount of p-toluene sulfonic acid along with molecular sieves and stirred at room temperature overnight. The added water and extracted 3 times with EtOAc. The organics were dried (MgSO4) and filtered off through a pad of Magnesol and concentrated in vacuo. to afford a solid. The solid was triturated with diethyl ether to give a white solid that was filtered and washed with diethyl ether to give (54 mg) MS m/z=476.2 (M+H).

Workup

  1. extractionThe added water and extracted 3 times with EtOAc
  2. dry with materialThe organics were dried (MgSO4)
  3. filtrationfiltered off through a pad of Magnesol
  4. concentrationconcentrated in vacuo
  5. customto afford a solid
  6. customThe solid was triturated with diethyl ether
  7. customto give a white solid
  8. filtrationthat was filtered
  9. washwashed with diethyl ether
  10. customto give (54 mg)

Sources & evidence

ORD record
ord-0574f33177414f839be0d3a47213a9af
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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