Water → HCID 86704020, compound

HRID 1773930Notes

Reaction equation

HRID 1773930 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:13]3[C:23]([OH:25])=[O:24])[CH2:4][CH2:3]1.[CH3:32][Si](C=[N+]=[N-])(C)C.O>CO.C(Cl)Cl>[CH3:32][O:24][C:23]([C:13]1[N:14]2[C:10]([CH:9]([O:8][CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15]2)=[N:11][C:12]=1[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:25]

Participants

6

Reactant 3

HCID 962WaterHCID 167693Trimethylsilyldiazomethane2×HCID 86704021HCID 86704021, compound

Product 1

HCID 86704020HCID 86704020, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid (example 256B) (50 mg, 0.120 mmole) in MeOH (2 mL) is added a 2M solution of trimethylsilyldiazomethane in CH2Cl2 (0.2 mL). After 2 hours, as the reaction is only partial, a 2M solution of trimethylsilyldiazomethane in CH2Cl2 (0.2 mL) is added and the reaction mixture is heated at 45° C. overnight. Water is added and the aqueous phase is extracted with AcOEt. The organic phase is dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH) from (100:0) to (95:5) to give 4-(1-methylpiperidin-4-yloxy)-2-phenyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid methyl ester.

Workup

  1. extractionthe aqueous phase is extracted with AcOEt
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with (CH2Cl2:MeOH) from (100:0) to (95:5)

Sources & evidence

ORD record
ord-ac8ae75926d04a34addc47bb5af29e21
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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