Potassium Carbonate → HCID 66758055, compound

HRID 917166Notes

Reaction equation

HRID 917166 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][N:10]([C@@H:12]3[CH2:16][CH2:15][NH:14][CH2:13]3)[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH:28]=[C:29]1[C:35]2[CH:36]=[CH:37][CH:38]=[N:39][C:34]=2[CH2:33][O:32][C:31]2[CH:40]=[CH:41][C:42]([C:44]([OH:47])([CH3:46])[CH3:45])=[CH:43][C:30]1=2>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][N:10]([C@@H:12]3[CH2:16][CH2:15][N:14]([CH2:26][CH2:27][CH:28]=[C:29]4[C:35]5[CH:36]=[CH:37][CH:38]=[N:39][C:34]=5[CH2:33][O:32][C:31]5[CH:40]=[CH:41][C:42]([C:44]([OH:47])([CH3:46])[CH3:45])=[CH:43][C:30]4=5)[CH2:13]3)[CH2:9][C:8](=[O:17])[NH:7][C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 666859992-[5-(3-Bromo-propylidene)-5,1 1-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-olHCID 66758277HCID 66758277, compound

Product 1

HCID 66758055HCID 66758055, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a solution of (R)-8-chloro-4-pyrrolidin-3-yl-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.198 g, 0.58 mmol) in acetonitrile/water (8:2) (5.8 mL) was added K2CO3 (0.655 g, 4.6 mmol) and 2-[5-(3-bromo-propylidene)-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yl]-propan-2-ol (0.183 g, 0.48 mmol). The solution was allowed to stir at room temperature for 48 h. The reaction was concentrated down and partitioned between EtOAc/H2O, extracted with EtOAc (3×). The organics were collected together dried over Mg2SO4, filtered and evaporated in vacuo, then purified by Biotage flash chromatography (5% methanol/95% methylene chloride to 10% methanol/90% methylene chloride to 15% methanol/85% methylene chloride) to yield the title compound (0.077 g, 28%). 1H-NMR (CDCl3): δ 1.55 (s, 6H), 1.74 (septet, 1H), 2.01 (sextet, 1H), 2.32–2.60 (m, 6H), 2.76 (t, 1H), 3.26 (pentet, 1H), 3.43 (d, 1H), 3.46 (s, 2H), 3.74 (s, 2H), 5.27 (bs, 2H), 6.12 (t, 1H), 6.78 (d, 1H), 6.96 (s, 1H), 7.06 (dd, 1H), 7.13 (d, 1H), 7.19–7.27 (m, 2H), 7.44 (d, 1H), 7.55 (dd, 1H), 8.47 (dd, 1H), 8.49 (s, 1H). ESI-MS m/z: 559 (M+1), retention time 1.24.

Workup

  1. concentrationThe reaction was concentrated down
  2. custompartitioned between EtOAc/H2O
  3. extractionextracted with EtOAc (3×)
  4. customThe organics were collected together
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. custompurified by Biotage flash chromatography (5% methanol/95% methylene chloride to 10% methanol/90% methylene chloride to 15% methanol/85% methylene chloride)

Sources & evidence

ORD record
ord-db6ad3ca48114e5780bab77481ae8a4c
Source dataset
uspto-grants-2007_09
Patent number
US07271176B2

Reaction notes

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