Dimethylformamide → HCID 10304923, compound

HRID 1830059Notes

Reaction equation

HRID 1830059 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]([O:18][CH3:19])=[C:4]([C:20](C2C=C(C(O)=O)N3CC4C=CC=CC=4NCC=23)=[O:21])[CH:3]=1.[CH3:39][NH:40][CH2:41][C:42]1[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=1.O[N:49]1[C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH:70]([N:73]([CH2:77]C)[CH:74]([CH3:76])[CH3:75])([CH3:72])[CH3:71].CN(C)C=[O:82]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])=[CH:6][C:5]([O:18][CH3:19])=[C:4]([C:20]([N:49]2[C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=3[CH2:77][N:73]3[C:70]([C:71]([N:40]([CH3:39])[CH2:41][C:42]4[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=4)=[O:82])=[CH:72][CH:75]=[C:74]3[CH2:76]2)=[O:21])[CH:3]=1

Participants

8

Reactant 6

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 883933-(Methylaminomethyl)pyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131725796HCID 131725796, compound

Product 1

HCID 10304923HCID 10304923, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of the 10-{[6-chloro-3-methoxy-2′-(trifluoromethyl)[1,1′-biphenyl]-4-yl]carbonyl-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid of Step D (0.250 g, 0.46 mmol) in N,N-dimethylformamide (2 mL) was added 3-(methylaminomethyl)pyridine (0.068 g, 0.55 mmol), 1-hydroxybenzotriazole (0.069 g, 0.51 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (0.087 g, 0.51 mmol), and N,N-diisopropylethyl amine (0.090 g, 0.69 mmol). After stirring overnight, the reaction mixture was taken up in chloroform, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered and evaporated to yield the title compound (0.153 g) as a solid which was recrystallized from ethyl acetate, m.p. 124–126° C. The sample was shown to be 93% pure by analytical HPLC [Primesphere C-18 column (2.0×150 mm); mobile phase: 45/55 acetonitrile/water containing 0.1% phosphoric acid].

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f7d846794f1940faa073f96f248d4edd
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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