Tetrahydrofuran → HCID 10009546, compound

HRID 644299Notes

Reaction equation

HRID 644299 reaction equation
[NH2:1][C@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH3:26])=[C:21]([CH2:27][CH3:28])[CH:20]=1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[NH:29]1[CH2:34][CH2:33][CH:32]([N:35]2[CH2:41][CH2:40][C:39]3[CH:42]=[CH:43][CH:44]=[CH:45][C:38]=3[NH:37][C:36]2=[O:46])[CH2:31][CH2:30]1.C1C[O:50][CH2:49]C1>CN(C=O)C>[CH2:27]([C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][C:22]=1[CH2:25][CH3:26])[CH2:18][C@@H:2]([NH:1][C:49]([N:29]1[CH2:30][CH2:31][CH:32]([N:35]2[CH2:41][CH2:40][C:39]3[CH:42]=[CH:43][CH:44]=[CH:45][C:38]=3[NH:37][C:36]2=[O:46])[CH2:33][CH2:34]1)=[O:50])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:12][CH2:13][N:14]([CH3:17])[CH2:15][CH2:16]2)[CH2:7][CH2:6]1)=[O:4])[CH3:28]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 113795873-(Piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 68578923HCID 68578923, compound

Product 1

HCID 10009546HCID 10009546, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.1 g (10.61 mmol) of (R)-2-amino-3-(3,4-diethyl-phenyl)-1-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-propan-1-one, dissolved in 50 mL of THF, were slowly added dropwise to the ice-cooled mixture of 150 mL of THF and 1.9 g (11.2 mmol) of CDT. Then the mixture was stirred for 30 min in the ice bath and for a further 45 min at RT before the solution of 2.7 g (11.0 mmol) of 3-piperidin-4-yl-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one in 20 mL of DMF was added and the mixture was refluxed for 4 h. The reaction mixture was evaporated down under reduced pressure, the residue was combined with Na2CO3 solution and exhaustively extracted with EtOAc. The combined organic extracts were washed with water, dried over Na2SO4, evaporated down and purified over aluminium oxide. The product was obtained as a solid.

Workup

  1. temperaturecooled
  2. additionwas added
  3. temperaturethe mixture was refluxed for 4 h
  4. customThe reaction mixture was evaporated down under reduced pressure
  5. extractionexhaustively extracted with EtOAc
  6. washThe combined organic extracts were washed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated down
  9. custompurified over aluminium oxide
  10. customThe product was obtained as a solid

Sources & evidence

ORD record
ord-312ad8e1c702423d9797450d3c7b2af1
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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