Bromide ion → HCID 86667379, compound

HRID 334168Notes

Reaction equation

HRID 334168 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH:17]([NH2:19])[CH3:18])[N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[N:3]=1.[Br-:26].C(N([CH2:32][CH3:33])CC)C.[OH2:34]>C(Cl)Cl>[Br:26][CH2:32][C:33]([NH:19][CH:17]([C:7]1[N:8]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[C:9]2[C:5]([N:6]=1)=[C:4]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[N:3]=[C:2]([Cl:1])[N:10]=2)[CH3:18])=[O:34]

Participants

6

Reactant 4

HCID 259Bromide ion2×HCID 962WaterHCID 8471TriethylamineHCID 86667378HCID 86667378, compound

Product 1

HCID 86667379HCID 86667379, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-ethylamine (0.25 g, 0.68 mmol) in anhydrous DCM were added romoacetyl bromide (62 μL, 0.74 mmol) and triethylamine (0.13 mL, 0.93 mmol). The mixture was stirred at RT. After 2 h, another portion of romoacetyl bromide (12 μL) was added and stirring continued for 1.5 h. Water was added, the phases were separated and the aqueous phase was extracted twice with DCM. The combined organic fractions were dried (Na2SO4), filtered and concentrated in vacuo to give 2-Bromo-N-{1-[2-chloro-6-morpholin-4-yl-9-(tetrahydro-pyran-2-yl)-9H-purin-8-yl]-ethyl}-acetamide (385 mg, mixture of two pairs of diastereomers), which was used in the next step without purification. LCMS RT=3.45 min and 3.52 min, [M+H]+=487/489/491

Workup

  1. stirringstirring
  2. waitcontinued for 1.5 h
  3. customthe phases were separated
  4. extractionthe aqueous phase was extracted twice with DCM
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a19a2dc20b2b41cf896223b3a404f7e3
Source dataset
uspto-grants-2014_11
Patent number
US08883799B2

Reaction notes

Loading…