Cesium carbonate → HCID 25270134, compound

HRID 469408Notes

Reaction equation

HRID 469408 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[NH:7][C:8](=[O:18])[N:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.Br[C:22]1[CH:23]=[C:24]([CH:39]=[CH:40][CH:41]=1)[C:25]([C:27]1[CH:37]=[C:36]([CH3:38])[C:30]2[N:31]([CH3:35])[C:32](=[O:34])[O:33][C:29]=2[CH:28]=1)=[O:26].C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:35][N:31]1[C:30]2[C:36]([CH3:38])=[CH:37][C:27]([C:25]([C:24]3[CH:39]=[C:40]([N:15]4[CH2:14][CH2:13][CH:12]([N:9]5[CH2:10][CH2:11][C:5]6[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:6]=6[NH:7][C:8]5=[O:18])[CH2:17][CH2:16]4)[CH:41]=[CH:22][CH:23]=3)=[O:26])=[CH:28][C:29]=2[O:33][C:32]1=[O:34]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 183568527-methoxy-3-(piperidin-4-yl)-4,5-dihydro-1H-benzo[d][1,3]diazepin-2(3H)-oneHCID 58181100HCID 58181100, compound

Product 1

HCID 25270134HCID 25270134, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

Under an argon atmosphere 330 mg (1.20 mmol) 7-methoxy-3-piperidin-4-yl-1,3,4,5-tetrahydro-benzo[d][1,3]diazepin-2-one, 350 mg (1.01 mmol) 6-(3-bromo-benzoyl)-3,4-dimethyl-3H-benzoxazol-2-one and 586 mg (1.80 mmol) caesium carbonate were stirred in 10 mL xylene, then combined with 56 mg (0.090 mmol) BINAP and 20 mg (0.089 mmol) palladium(II)acetate and stirred for 48 h at 100° C. The mixture was evaporated down i. vac., the residue was dissolved in DMF/MeOH and purified by preparative HPLC-MS. The fractions containing the product were combined and the acetonitrile was evaporated down. The aqueous residue was made basic with 1N aqueous sodium hydroxide solution, the precipitate formed was suction filtered and washed with water and dried. The product was again purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. customThe mixture was evaporated down i
  2. dissolution, the residue was dissolved in DMF/MeOH
  3. custompurified by preparative HPLC-MS
  4. additionThe fractions containing the product
  5. customthe acetonitrile was evaporated down
  6. customthe precipitate formed
  7. filtrationfiltered
  8. washwashed with water
  9. customdried
  10. customThe product was again purified by preparative HPLC-MS
  11. additionThe fractions containing the product
  12. customfreeze-dried

Sources & evidence

ORD record
ord-138456080faf46eb8524d51fd0dd9d16
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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