Oxalyl chloride → HCID 66678401, compound

HRID 219955Notes

Reaction equation

HRID 219955 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].[NH2:26][C:27](=[N:40]O)[C:28]1[C:37]([F:38])=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[C:30]([F:39])[CH:29]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.C1COCC1.CN(C=O)C>[F:39][C:30]1[CH:29]=[C:28]([C:27]2[N:26]=[C:16]([C:14]3[CH:13]=[CH:12][C:11]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH3:25])=[C:10]([CH2:9][O:8][CH3:7])[CH:15]=3)[O:18][N:40]=2)[C:37]([F:38])=[CH:36][C:31]=1[C:32]([O:34][CH3:35])=[O:33]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 594958222-(Methoxymethyl)-2'-methylbiphenyl-4-carboxylic acidHCID 72307495HCID 72307495, compound

Product 1

HCID 66678401HCID 66678401, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Oxalyl chloride (190.39 mg; 1.50 mmol; 3 eq.) was added to a suspension of Intermediate 28 (143.64 mg; 0.50 mmol; 1 eq.) and DMF (cat.) in DCM (2 mL) and the resulting mixture was stirred at RT for 1 hour. After evaporation to dryness, the residue was taken up in THF (2 mL) and added to solution of Intermediate 52 (108.62 mg; 0.50 mmol; 1 eq.) and DIEA (193.87 mg; 1.50 mmol; 3 eq.) in THF (1 mL). The resulting mixture was heated to 150° C. for 30 minutes in the microwave. It was then filtered through a SPE-NH2 column, which was further washed with THF. After evaporation, the residue was purified by FC(C-Hex/EtOAc 9:1 until 5:5), affording the title product as a off-white solid. LC/MS (Method B): 451.2 (M+H)+. HPLC (Method A) Rt 6.0 min (Purity: 89.6%).

Workup

  1. customAfter evaporation to dryness
  2. temperatureThe resulting mixture was heated to 150° C. for 30 minutes in the microwave
  3. filtrationIt was then filtered through a SPE-NH2 column, which
  4. washwas further washed with THF
  5. customAfter evaporation
  6. customthe residue was purified by FC(C-Hex/EtOAc 9:1 until 5:5)

Sources & evidence

ORD record
ord-f32348337a6a4fd390f8fc205ea9cae1
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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