Acetic Anhydride → HCID 18932748, compound

HRID 1597970Notes

Reaction equation

HRID 1597970 reaction equation
[C:1](OC(=O)C)(=[O:3])C.Cl.[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[N:23]1[C:31]2[C:26](=[CH:27][C:28]([NH2:32])=[CH:29][CH:30]=2)[CH2:25][CH2:24]1>C(O)=O>[CH3:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][C:20]=1[O:21][CH3:22])[N:17]=[CH:16][N:15]=[C:14]2[N:23]1[C:31]2[C:26](=[CH:27][C:28]([NH:32][CH:1]=[O:3])=[CH:29][CH:30]=2)[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67651584HCID 67651584, compound

Product 1

HCID 18932748HCID 18932748, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
5 °C

Procedure

Formic acid (42 μL) was added to acetic anhydride (88 μL) while stirring at 5° C. and the mixture was allowed to stir at 20° C. for 1 hour before adding 1-(6,7-dimethoxy-quinazolin-4-yl)-2,3-dihydro-1H-indol-5-ylamine (102 mg, 0.316 mmol; freebase from Example 83). The mixture was stirred at 20° C. for 1.5 hours, quenched with H2O (5 mL), stirred 30 min. and diluted with CHCl3 (15 mL). The organic phase was separated and washed with saturated aqueous NaHCO3, dried over Na2 SO4(s), filtered and concentrated in vacuo. Flash chromatography on silica (4% MeOH/CH2Cl2) afforded 66 mg of product. (M.P. 239°-244° C. (dec); LC-MS: 351 (MH+); anal. RP18-HPLC RT: 2.92 min.).

Workup

  1. stirringto stir at 20° C. for 1 hour
  2. stirringThe mixture was stirred at 20° C. for 1.5 hours
  3. customquenched with H2O (5 mL)
  4. stirringstirred 30 min.
  5. additiondiluted with CHCl3 (15 mL)
  6. customThe organic phase was separated
  7. washwashed with saturated aqueous NaHCO3
  8. customdried over Na2 SO4(s)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ad33c2333c5478a9e7828572d0ae7e7
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

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