Dimethyl Sulfoxide → HCID 178430863, compound

HRID 2091689Notes

Reaction equation

HRID 2091689 reaction equation
CS(C)=O.C(Cl)Cl.C(Cl)(=O)C(Cl)=O.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]1[C:23]([C:39]#[N:40])=[C:24]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[S:25][C:26]=1[C:27]1[NH:28][CH2:29][CH:30]([CH3:32])[N:31]=1.[OH-].[NH4+]>>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]1[C:23]([C:39]#[N:40])=[C:24]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[S:25][C:26]=1[C:27]1[NH:28][CH:29]=[C:30]([CH3:32])[N:31]=1

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 178430462HCID 178430462, compound

Product 1

HCID 178430863HCID 178430863, compoundYield 21.4%

Procedure

To DMSO (32.0 uL, 0.000451 mol) in DCM (3 mL, 0.05 mol) at −78° C. was added oxalyl chloride (38.2 uL, 0.000451 mol) and the mixture was stirred for 30 min. 4-(2,4-dichlorophenyl)-5-(4-methyl-4,5-dihydro-1H-imidazol-2-yl)-2-morpholinothiophene-3-carbonitrile (19 mg, 0.000045 mol) in DCM (1.5 mL, 0.023 mol) was added. After 1 h, TEA (0.188 mL, 0.00135 mol) was added and the mixture was stirred for another 30 min. 33% ammonium hydroxide (33:67, ammonia:Water, 0.117 mL) was added and the reaction mixture was warmed to room temperature. The mixture was purified by column chromatography to afford 4-(2,4-dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)-2-morpholinothiophene-3-carbonitrile (4.04 mg, 21%). LCMS: (FA) ES+ 419.13, ES− 417.17. 1H NMR (400 MHz, d1-chloroform) δ: 7.61 (d, 1H), 7.42 (dd, 1H), 7.34 (d, 1H), 6.61 (s, 1H), 3.88-3.84 (m, 4H), 3.62-3.57 (m, 4H), 2.21 (s, 3H).

Workup

  1. waitAfter 1 h
  2. stirringthe mixture was stirred for another 30 min
  3. customThe mixture was purified by column chromatography

Sources & evidence

ORD record
ord-381645eb75ab45418b1138c5b282690c
Source dataset
uspto-grants-2013_05
Patent number
US08440664B2

Reaction notes

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