Acetic Anhydride → HCID 18932899, compound

HRID 1597969Notes

Reaction equation

HRID 1597969 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][N:8]=[C:7]2[N:16]1[C:24]2[C:19](=[CH:20][C:21]([NH2:25])=[CH:22][CH:23]=2)[CH2:18][CH2:17]1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[O:14][CH3:15])[N:10]=[CH:9][N:8]=[C:7]2[N:16]1[C:24]2[C:19](=[CH:20][C:21]([NH:25][C:26](=[O:28])[CH3:27])=[CH:22][CH:23]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 67651584HCID 67651584, compound

Product 1

HCID 18932899HCID 18932899, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-5-ylamine (102 mg, 0.316 mmol; free-base from Example 83) and 4-(N,N-dimethylamino)pyridine (51.2 mg, 0.42 mmol) in CH2Cl2 (5 mL) was added acetic anhydride (88 μL, 0.93 mmol). The mixture was stirred at 20° C. for 7.5 hours, quenched with H=O (5 mL), stirred 30 min. and diluted with CHCl3 (15 mL). The organic phase was separated and washed with saturated aqueous NaHCO3, dried over Na2SO4(s), filtered and concentrated in vacuo. Flash chromatography on silica (3.5% MeOH/CHCl3) afforded 53 mg of product. (M.P. >250° C. (dec); LC-MS: 365 (MH+); anal. RP18-HPLC RT: 2.79 min.).

Workup

  1. customquenched with H=O (5 mL)
  2. stirringstirred 30 min.
  3. additiondiluted with CHCl3 (15 mL)
  4. customThe organic phase was separated
  5. washwashed with saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4(s)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5546d6f9c2ff40f28dbfd2d47ab73bb1
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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