Acetyl chloride → HCID 21101584, compound

HRID 1353330Notes

Reaction equation

HRID 1353330 reaction equation
C([O:5][C:6]([NH:8][C:9]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[O:26])[CH2:21][CH2:20]2)[C:16]2[C:11](=[CH:12][C:13]([Cl:35])=[CH:14][CH:15]=2)[N:10]=1)=O)(C)(C)C.F[C:37](F)(F)C(O)=O.C(N(CC)CC)C.C(Cl)(=O)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:6]([NH:8][C:9]1[CH:18]=[C:17]([N:19]2[CH2:20][CH2:21][N:22]([C:25]([NH:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[O:26])[CH2:23][CH2:24]2)[C:16]2[C:11](=[CH:12][C:13]([Cl:35])=[CH:14][CH:15]=2)[N:10]=1)(=[O:5])[CH3:37]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 21101591HCID 21101591, compound

Product 1

HCID 21101584HCID 21101584, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2-tert-Butoxycarbonylamino-7-chloro-4-[4-(4-fluorophenylaminocarbonyl)piperazin-1-yl]quinoline (110 mg, 0.22 mmol) in CH2Cl2 (1 mL) is treated with trifluoroacetic acid (1 mL) for 2 h at room temp. The reaction mixture is concentrated. The residue is dissolved in CH2Cl2 (9 mL). Triethylamine (154 μL, 1.1 mmol), acetyl chloride (26 μL, 0.24 mmol), and DMAP (10 mg) are added. The reaction mixture is stirred at room temp. for 3 h, washed with water, dried (MgSO4), and concentrated. Purification of the residue by column chromatography with CH2Cl2-MeOH affords the title product.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. dissolutionThe residue is dissolved in CH2Cl2 (9 mL)
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the residue by column chromatography with CH2Cl2-MeOH

Sources & evidence

ORD record
ord-cb5c99020b25409db45bcba40c79d419
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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