Chloroform → HCID 58608146, compound

HRID 2243586Notes

Reaction equation

C([N:8]1[CH:13]=[CH:12][C:11](=O)[C:10]2[C:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:16]([C:18]3[CH:19]=C([CH:24]=[CH:25][CH:26]=3)C(O)=O)[O:17][C:9]1=2)C1C=CC=CC=1.[C:33](Cl)(=[O:37])[C:34](Cl)=O.[CH3:39][N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.CCN(CC)CC.C(Cl)(Cl)[Cl:54]>C(Cl)Cl.CN(C=O)C>[Cl:54][C:11]1[CH:12]=[CH:13][N:8]=[C:9]2[O:17][C:16]([C:18]3[CH:19]=[C:34]([C:33]([N:43]4[CH2:44][CH2:45][N:40]([CH3:39])[CH2:41][CH2:42]4)=[O:37])[CH:24]=[CH:25][CH:26]=3)=[C:15]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:10]=12

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of acid 4k (2.42 g, 5.75 mmol, 1.0 equiv) in CHCl3 (30 mL) was added oxalyl chloride (2.5 mL, 28.7 mmol, 5.0 equiv) followed by DMF (ca. 40 μL). The mixture was heated to 65° C. After 3 hr, the solvent was removed in vacuo and the resulting residue was taken up in CH2Cl2 (20 mL). 1-Methylpiperazine (1.3 mL, 11.5 mmol, 2.0 equiv) was added followed by Et3N (0.80 mL, 5.75 mmol, 1.0 equiv) and the solution was stirred at ambient temperature for 3 h. The solution was diluted with CH2Cl2 (20 mL) and washed with H2O and brine. After drying with MgSO4 and concentration in vacuo, the residue was purified by silica gel chromatography (5% MeOH:CH2Cl2) to provide chloride 61. MS (MH+) 432; Calculated 431.1 for C25H22ClN3O2.

Workup

customthe solvent was removed in vacuo
washwashed with H2O and brine
dry with materialAfter drying with MgSO4 and concentration in vacuo
customthe residue was purified by silica gel chromatography (5% MeOH:CH2Cl2)

Sources & evidence

ORD record: ord-48f0e562fd294b02b4c5af8e58e739ed
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674907B2

Reaction notes

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