Acetic Anhydride → HCID 22390556, compound

HRID 1072081Notes

Reaction equation

HRID 1072081 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:17]=[CH:18][N:19]3[C:24]=2[C:23]([NH:25][C:26]2[CH:27]=[C:28]4[C:32](=[CH:33][CH:34]=2)[N:31]([CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([F:42])[CH:37]=2)[N:30]=[CH:29]4)=[N:22][CH:21]=[N:20]3)[CH2:11][CH2:10]1.C([O-])([O-])=O.[K+].[K+]>CO>[F:42][C:38]1[CH:37]=[C:36]([CH:41]=[CH:40][CH:39]=1)[CH2:35][N:31]1[C:32]2[C:28](=[CH:27][C:26]([NH:25][C:23]3[C:24]4=[C:16]([CH2:15][N:12]5[CH2:11][CH2:10][CH:9]([NH:8][C:5](=[O:7])[CH3:6])[CH2:14][CH2:13]5)[CH:17]=[CH:18][N:19]4[N:20]=[CH:21][N:22]=3)=[CH:34][CH:33]=2)[CH:29]=[N:30]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 10151881HCID 10151881, compound

Product 1

HCID 22390556HCID 22390556, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic anhydride (25 uL, 2.3 equiv.) was added to a mixture of [5-(4-amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (47 mg, 0.1 mmole) and K2CO3 (21 mg 0.15 mmole) in MeOH (3 mL) at 0° C. under nitrogen. After 1 h, the reaction was removed from the ice bath and the mixture was left stirred at RT overnight. The solvent was removed and the residue was taken up in DCM, washed with water and dried (Na2SO4). Removal of the solvent followed by radial chromatography (2 mm silica gel plate, gradient elution with DCM containing 0 to 3% MeOH) afforded the title compound as a solid (41 mg, 80%). MS: 513 (M+H)+; HPLC Ret Time: 1.12 min (Xterra 3.0×50 mm S7 C18 column, 2 min gradient, 5 mL/min).

Workup

  1. customthe reaction was removed from the ice bath
  2. waitthe mixture was left
  3. customThe solvent was removed
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent
  7. washfollowed by radial chromatography (2 mm silica gel plate, gradient elution with DCM containing 0 to 3% MeOH)

Sources & evidence

ORD record
ord-38d7fdc292c84553a9a8c9548352c584
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

Loading…