Acetic Anhydride → HCID 59851270, compound

HRID 545002Notes

Reaction equation

HRID 545002 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24](I)[CH:25]=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C[C:30]([O:32]C(C)=O)=[O:31].C(O[Li])=O.[Li+].[Cl-].CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[N:13]=[CH:14][C:15]3[CH2:21][C:20](=[O:22])[NH:19][C:18]4[CH:23]=[C:24]([C:30]([OH:32])=[O:31])[CH:25]=[CH:26][C:17]=4[C:16]=3[N:28]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

10

Reactant 5

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 433294Lithium ChlorideHCID 56946380HCID 56946380, compoundHCID 178506946HCID 178506946, compound

Product 1

HCID 59851270HCID 59851270, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(3,4-dimethoxy-phenylamino)-9-iodo-5H,7H-benzo[b]pyrimido[4,5-d]azepin-6-one (I-30) (0.60 g, 1.20 mmol) in dry DMF (8 mL) was added Ac2O (0.23 mL, 2.44 mmol), HCOOLi (0.19 g, 3.66 mmol), LiCl (0.155 g, 3.66 mmol), and Pd(OAc)2 (0.01 g, 0.06 mmol). Lastly, i-Pr2NEt (0.42 mL, 2.44 mmol) was added and the mixture heated for 16 h at 80° C. in a sealed tube. The reaction mixture was then diluted with CH2Cl2 (30 mL), and the organic layer was washed with H2O (3×30 mL), dried over MgSO4, filtered and concentrated in vacuo to give crude product as a yellow solid. The solid was treated with EtOAc and sonicated to provide a white solid which was collected by filtration to provide I-53 (0.33 g, 71%): HRMS Calcd. for C21H18N4O5: 407.1355, Found 407.1364.

Workup

  1. washthe organic layer was washed with H2O (3×30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give crude product as a yellow solid
  6. customsonicated
  7. customto provide a white solid which
  8. filtrationwas collected by filtration
  9. customto provide I-53 (0.33 g, 71%)

Sources & evidence

ORD record
ord-f3d57b05b70d44b58831dc7f56c385c2
Source dataset
uspto-grants-2011_05
Patent number
US07935694B2

Reaction notes

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