Triethylamine → HCID 72694265, compound

HRID 1773874Notes

Reaction equation

HRID 1773874 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:23]2[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=2)=[CH:13]3)[CH2:4][CH2:3]1.CCN(CC)CC.[C:37](Cl)(=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39]>C(Cl)Cl>[CH3:39][C:38]([CH3:41])([CH3:40])[C:37]([NH:29][C:26]1[CH:25]=[CH:24][C:23]([C:12]2[N:11]=[C:10]3[N:14]([CH2:15][CH2:16][C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[CH:9]3[O:8][CH:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[CH:13]=2)=[CH:28][CH:27]=1)=[O:42]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 867039544-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylamine

Product 1

HCID 72694265HCID 72694265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylamine (example 16A) (100 mg, 0.258 mmole) in CH2Cl2 (2 mL) is added NEt3 (72 μL, 0.515 mmole) and pivaloylchloride (48 μL, 0.387 mmole). The reaction mixture is stirred at room temperature overnight. Solvent is removed under reduced pressure. AcOEt is added to the residue and the organic phase is washed with water and dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH) as eluent with a gradient from (100:0) to (90:10) to afford 2,2-dimethyl-N-{4-[4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenyl}-propionamide melting at 120° C.

Workup

  1. customSolvent is removed under reduced pressure
  2. additionAcOEt is added to the residue
  3. washthe organic phase is washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure
  7. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-6d2c20aa035b4c43a8d7d154fac64d67
Source dataset
uspto-grants-2016_02
Patent number
US09255101B2

Reaction notes

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