Dimethylformamide → HCID 10282918, compound

HRID 1830099Notes

Reaction equation

HRID 1830099 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([OH:11])=O)[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21].[C:24](Cl)(=O)C(Cl)=O.[CH:30]1[CH:31]=[CH:32][N:33]2[CH2:39][C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=3[NH:36][CH2:35][C:34]=12.CC[N:46]([CH:50]([CH3:52])C)[CH:47]([CH3:49])C.[CH3:53][N:54]([CH3:57])[CH:55]=[O:56]>CCCCCC.C(OCC)(=O)C>[CH3:13][O:12][C:6]1[CH:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:22])([F:21])[F:23])[C:3]([O:2][CH3:1])=[CH:8][C:7]=1[C:9]([N:36]1[C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[CH2:39][N:33]2[C:32]([C:55]([N:54]([CH3:57])[CH2:53][C:52]3[CH:50]=[N:46][CH:47]=[CH:49][CH:24]=3)=[O:56])=[CH:31][CH:30]=[C:34]2[CH2:35]1)=[O:11]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1554704810,11-Dihydro-5H-benzo[e]pyrrolo[1,2-a][1,4]diazepineHCID 21947847HCID 21947847, compound

Product 1

HCID 10282918HCID 10282918, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

The title compound was prepared in the manner of Example 19, Step A using 2,5-dimethoxy-2′-trifluoromethyl-[1,1′-biphenyl]-4-carboxylic acid of Step A (1.63 g, 5 mmol), oxalyl chloride (700 μL, 8 mmol), N,N-dimethylformamide (10 μL), 10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine (0.93 g, 5 mmol) and Hünig's base (1.78 ml, 10 mmol). Flash chromatography over silica gel using a solvent gradient from 30% ethyl acetate in hexane to 100% ethyl acetate provided the title compound (0.900 g) as a solid. Recrystallization from acetone/hexane yielded white needles, m.p. 210–213° C.

Sources & evidence

ORD record
ord-c0ab6cac998e4450939743a66ac8313d
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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