Triethylamine → HCID 86653764, compound

HRID 2189115Notes

Reaction equation

HRID 2189115 reaction equation
[CH3:1][O:2][C:3](=[O:7])[CH2:4][CH2:5]Br.C(N(CC)CC)C.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:31]3[C:30]([NH:32][CH:33]4[CH2:38][CH2:37][CH2:36][NH:35][CH2:34]4)=[N:29][CH:28]=[N:27][C:26]=3[O:25][C:24]=2[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:19][CH:18]=1>C1COCC1.ClCCl>[CH3:1][O:2][C:3](=[O:7])[CH:4]([N:35]1[CH2:36][CH2:37][CH2:38][CH:33]([NH:32][C:30]2[C:31]3[C:23]([C:20]4[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=4)=[C:24]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[O:25][C:26]=3[N:27]=[CH:28][N:29]=2)[CH2:34]1)[CH3:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76934Methyl 3-bromopropanoateHCID 58280153HCID 58280153, compound

Product 1

HCID 86653764HCID 86653764, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

Add 82 μl (0.749 mmol) of 3-bromopropanoic acid methyl ester and 104 μl (0.749 mmol) of triethylamine to a solution of 150 mg (0.375 mmol) of (+/−)-5-(4-methoxyphenyl)-6-phenyl-N-piperidin-3-ylfuro[2,3-d]pyrimidin-4-amine (Example 39A) in 0.75 ml of THF, and stir at 20-40° C. overnight. Dilute the mixture with dichloromethane and wash with saturated sodium hydrogencarbonate solution. After concentration under reduced pressure, stir the residue with methanol, filter off the precipitated product with suction and dry under high vacuum. Isolate a second product batch from the filtrate after concentration by preparative RP-HPLC (eluent: acetonitrile/water gradient). A total of 124 mg (67.1% of theory) of the target product are obtained.

Workup

  1. washwash with saturated sodium hydrogencarbonate solution
  2. concentrationAfter concentration under reduced pressure
  3. stirringstir the residue with methanol
  4. filtrationfilter off the precipitated product with suction
  5. customdry under high vacuum
  6. customIsolate a second product batch from the filtrate
  7. concentrationafter concentration by preparative RP-HPLC (eluent: acetonitrile/water gradient)
  8. customA total of 124 mg (67.1% of theory) of the target product are obtained

Sources & evidence

ORD record
ord-1daeb48272e84ab790a68461f22efbc5
Source dataset
uspto-grants-2012_12
Patent number
US08324222B2

Reaction notes

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