Dimethyl Sulfoxide → HCID 86609046, compound

HRID 2246849Notes

Reaction equation

HRID 2246849 reaction equation
ClC(Cl)(Cl)[C:3]([C:5]1[N:14]2[C:8]([CH2:9][N:10]([C:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH3:33])=[C:23]([CH3:34])[CH:22]=3)=[O:20])[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13]2)=[CH:7][CH:6]=1)=[O:4].[C:37]([O:41][C:42]([N:44]1[CH2:49][CH2:48][CH2:47][CH:46]([CH2:50][NH2:51])[CH2:45]1)=[O:43])([CH3:40])([CH3:39])[CH3:38].CS(C)=O>C(#N)C.ClCCl>[CH3:34][C:23]1[CH:22]=[C:21]([C:19]([N:10]2[C:11]3[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=3[CH2:13][N:14]3[C:5]([C:3]([NH:51][CH2:50][CH:46]4[CH2:47][CH2:48][CH2:49][N:44]([C:42]([O:41][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:43])[CH2:45]4)=[O:4])=[CH:6][CH2:7][C:8]3=[CH:9]2)=[O:20])[CH:26]=[CH:25][C:24]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[CH3:33]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 27564831-Boc-3-(aminomethyl)piperidineHCID 160384712,2,2-Trichloro-1-{10-[(2,2'-dimethyl-1,1'-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone

Product 1

HCID 86609046HCID 86609046, compoundYield 128%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2,2,2-trichloro-1-{10-[(2,2′-dimethyl-1,1′-biphenyl-4-yl)carbonyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl}ethanone of Example 9 (0.54 g, 1.0 mmol) and 3-aminomethyl-piperidine-1-carboxylic acid tert-butyl ester (0.43 g, 2.0 mmol) in dry acetonitrile (5 mL) was added dimethylsulfoxide (0.35 mL, 4.9 mmol) and the reaction mixture heated to 80° C. under nitrogen for 3 days. The cooled reaction mixture was diluted with dichloromethane (25 mL), washed with water (2×25 mL) and brine (25 mL), dried over anhydrous potassium carbonate, filtered and concentrated in vacuo to afford a brown oil (0.81 g). Purification by flash chromatography using a solvent gradient of 3 to 20% ethyl acetate in dichloromethane gave the title compound (0.45 g) as a white foam.

Workup

  1. customThe cooled reaction mixture
  2. washwashed with water (2×25 mL) and brine (25 mL)
  3. dry with materialdried over anhydrous potassium carbonate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0cd3c97f67554a5ca1379ae67c8087ae
Source dataset
uspto-grants-2010_03
Patent number
US07687623B2

Reaction notes

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