HCID 58181124, compound → HCID 25267680, compound

HRID 469440Notes

Reaction equation

HRID 469440 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]2[NH:7][C:8](=[O:19])[N:9]([CH:12]3[CH2:17][CH2:16][NH:15][CH:14]([CH3:18])[CH2:13]3)[CH2:10][CH2:11][C:5]=2[CH:4]=1.Cl[C:23]1[N:28]=[CH:27][N:26]=[C:25]([C:29]([C:31]2[CH:41]=[C:40]([CH3:42])[C:34]3[N:35]([CH3:39])[C:36](=[O:38])[O:37][C:33]=3[CH:32]=2)=[O:30])[CH:24]=1>CN(C=O)C>[CH3:39][N:35]1[C:34]2[C:40]([CH3:42])=[CH:41][C:31]([C:29]([C:25]3[N:26]=[CH:27][N:28]=[C:23]([N:15]4[CH2:16][CH2:17][CH:12]([N:9]5[CH2:10][CH2:11][C:5]6[CH:4]=[C:3]([O:2][CH3:1])[CH:21]=[CH:20][C:6]=6[NH:7][C:8]5=[O:19])[CH2:13][CH:14]4[CH3:18])[CH:24]=3)=[O:30])=[CH:32][C:33]=2[O:37][C:36]1=[O:38]

Participants

4

Reactant 2

HCID 58181124HCID 58181124, compound2×HCID 581811626-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Product 1

HCID 25267680HCID 25267680, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 mg (0.21 mmol) 7-methoxy-3-(2-methyl-piperidin-4-yl)-1,3,4,5-tetrahydro-benzo[d]-[1,3]diazepin-2-one, 60 mg (0.20 mmol) 6-(6-chloropyrimidine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and 0.040 mL (0.29 mmol) TEA were combined in 1 mL DMF and stirred for three days at RT. Then 7-methoxy-3-(2-methyl-piperidin-4-yl)-1,3,4,5-tetrahydrobenzo[d][1,3]diazepin-2-one was added again and the mixture was stirred for 3 h at 80° C. The reaction mixture was purified by preparative HPLC. The fractions containing the product were combined and the solvent was evaporated down by half. The aqueous residue was extracted with DCM, the combined organic phases were dried on sodium sulphate, filtered and the filtrate was evaporated down.

Workup

  1. stirringthe mixture was stirred for 3 h at 80° C
  2. customThe reaction mixture was purified by preparative HPLC
  3. additionThe fractions containing the product
  4. customthe solvent was evaporated down by half
  5. extractionThe aqueous residue was extracted with DCM
  6. customthe combined organic phases were dried on sodium sulphate
  7. filtrationfiltered
  8. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-19627aa16acf4d38b0e8b469074848b9
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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