Pyridine → HCID 19957031, compound

HRID 1769145Notes

Reaction equation

HRID 1769145 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][NH:14][C:13]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=3)=[N:12]2)=[CH:7][CH:6]=1.N1C=CC=CC=1.[CH3:37][S:38]([Cl:41])(=[O:40])=[O:39].[C:42]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[ClH:41].[CH3:42][N:14]1[C:13]([CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH:30][S:38]([CH3:37])(=[O:40])=[O:39])=[CH:28][CH:29]=2)=[N:12][CH:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 178488941HCID 178488941, compound

Product 1

HCID 19957031HCID 19957031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of the amine of Example 384 (b) (3.33 g, 7.3 mmol) in CH2Cl2 (35 mL) was added pyridine (17 mL), followed by methanesulfonyl chloride (0.84 mL) in CH2Cl2 (10 mL). The mixture was warmed to room temperature, stirred for 1.5 hours, and poured into saturated K2CO3 (50 mL). The organic layer was separated and the precipitate which formed over 2 hours was collected by filtration. The solid was converted into the fumarate salt, which was purified by column chromatography on neutral alumina eluting with 5-6% methanol in CH2Cl2. The purified salt was then converted back into the free base and then into the hydrochloride salt to afford 1.224 g of 4,5-dihydro-4-methyl-1-(4-methoxyphenyl)-3-[2-(4-methylsulfonylaminophenyl)ethyl]-1H-2,4-benzodiazepine hydrochloride as a light yellow powder, m.p. 149° C. (dec.).

Workup

  1. customThe organic layer was separated
  2. customthe precipitate which formed over 2 hours
  3. filtrationwas collected by filtration
  4. customwas purified by column chromatography on neutral alumina eluting with 5-6% methanol in CH2Cl2

Sources & evidence

ORD record
ord-c6be12440261471a9b9bdd5f9677b7ed
Source dataset
uspto-grants-1995_01
Patent number
US05380721

Reaction notes

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