Water → HCID 178465002, compound

HRID 334169Notes

Reaction equation

HRID 334169 reaction equation
[Br:1][CH2:2][C:3]([NH:5][CH:6]([C:8]1[N:9](C2CCCCO2)[C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[N:13]=[C:12]([Cl:23])[N:11]=2)[CH3:7])=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O.C(=O)(O)[O-].[Na+]>CO>[Br:1][CH2:2][C:3]([NH:5][CH:6]([C:8]1[NH:9][C:10]2[C:15]([N:16]=1)=[C:14]([N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)[N:13]=[C:12]([Cl:23])[N:11]=2)[CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86667379HCID 86667379, compound

Product 1

HCID 178465002HCID 178465002, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Bromo-N-{1-[2-chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-ethyl}-acetamide (crude from step 5, 385 mg) was dissolved in methanol (15 mL) and p-toluenesulfonic acid monohydrate (35 mg) was added. The mixture was stirred at RT for 16 h. Water was added, aqueous sodium bicarbonate was added to give pH 7 and the precipitate was filtered off, washed with water and dried (in vacuo, 50° C.) to give 2-Bromo-N-[1-(2-chloro-6-morpholin-4-yl-9H-purin-8-yl)-ethyl]-acetamide (207 mg, 76%). The aqueous filtrate was extracted three times with ethyl acetate. The organic layer was separated and dried (Na2SO4), then concentrated in vacuo to afford a further crop of less pure 2-Bromo-N-[1-(2-chloro-6-morpholin-4-yl-9H-purin-8-yl)-ethyl]-acetamide (39 mg). LCMS RT=2.57 min, [M+H]+=403/405/407

Workup

  1. customto give pH 7
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. customdried (in vacuo, 50° C.)

Sources & evidence

ORD record
ord-ede585c2f93742fabb0b336ba54dde8c
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

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