Dimethyl Sulfoxide → HCID 11954415, compound

HRID 2246840Notes

Reaction equation

HRID 2246840 reaction equation
[CH3:1][NH2:2].ClC(Cl)(Cl)[C:5]([C:7]1[N:16]2[C:10]([CH2:11][N:12]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:25][CH:24]=3)=[O:22])[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH2:15]2)=[CH:9][CH:8]=1)=[O:6].C(N([CH2:44][CH3:45])CC)C.CS(C)=O>C(#N)C>[CH3:31][C:30]1[O:35][C:44]([CH3:45])=[CH:26][C:29]=1[CH2:1][NH:2][C:5]([C:7]1[N:16]2[C:10]([CH2:11][N:12]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:25][CH:24]=3)=[O:22])[C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[CH2:15]2)=[CH:9][CH:8]=1)=[O:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6329MethylamineHCID 8471TriethylamineHCID 160384072,2,2-trichloro-1-{10-[(2'-methoxy-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 11954415HCID 11954415, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared according to the procedure of Example 2 starting from 2,5-dimethyl-3-furyl)methylamine (0.264 g, 2.1 mmole), 2,2,2-trichloro-1-{10-[(2′-methoxy-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 1 (1.138 g, 2.1 mmole), triethylamine (0.470 g, 2.2 eq., 4.6 mmole) and dimethylsulfoxide (1.1 g, 5.0 eq., 10.5 mmole) in 20 mL of acetonitrile. Flash chromatography of the residue on silica Merck-60 using a gradient elution of 30 to 45% ethyl acetate in hexane gave a white powder (0.453 g). Further purification was achieved by prep HPLC, Primesphere C18, 2×25 cm column, 68% acetonitrile in water containing trifluoroacetic acid, 100 ml/min, 254 nm detection. The pure fractions were neutralized with ammonium hydroxide and evaporated to an amorphous solid (0.153 g).

Workup

  1. washa gradient elution of 30 to 45% ethyl acetate in hexane

Sources & evidence

ORD record
ord-6eaf77880a4b4fe88d2e5142b9bc4b0f
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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