Isopropanol → HCID 57920207, compound

HRID 216052Notes

Reaction equation

HRID 216052 reaction equation
[CH3:1][N:2]([CH3:28])[C:3](=[O:27])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:13])[CH:6]=1.Cl[C:30]1[C:31]2[C:38]([CH3:39])=[CH:37][NH:36][C:32]=2[N:33]=[CH:34][N:35]=1.C(N(CC)C(C)C)(C)C.C(O)(C)C>C(Cl)Cl>[CH3:28][N:2]([CH3:1])[C:3](=[O:27])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([C:14]2([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][CH2:16][N:17]([C:30]3[C:31]4[C:38]([CH3:39])=[CH:37][NH:36][C:32]=4[N:33]=[CH:34][N:35]=3)[CH2:18][CH2:19]2)=[O:13])[CH:6]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 148092824-Chloro-5-methyl-7H-pyrrolo(2,3-d)pyrimidineHCID 67036873HCID 67036873, compound

Product 1

HCID 57920207HCID 57920207, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

3-(4-benzylpiperidine-4-carboxamido)phenyl dimethylcarbamate (0.140 g, 0.336 mmol) from step B, 4-chloro-5-methyl-7H-pyrrolo[2,3-d]pyrimidine (0.056 g, 0.336 mmol), N,N-diisopropylethylamine (0.175 mL, 1.00 mmol), and isopropanol (5 mL) were combined and heated at 120° C. overnight in a pressure vessel. The reaction was diluted with CH2Cl2, washed with H2O and brine, dried over MgSO4, and concentrated under vacuum. The residue was taken up in hot ethanol/H2O. Upon cooling, the product precipitated out of solution to give the title compound in 81% yield.

Workup

  1. washwashed with H2O and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under vacuum
  4. temperatureUpon cooling
  5. customthe product precipitated out of solution

Sources & evidence

ORD record
ord-668e2089f0194c2996fe99880571f8bb
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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