Dimethylformamide → HCID 58095257, compound

HRID 2402469Notes

Reaction equation

HRID 2402469 reaction equation
[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[C:6]([C:16]2[NH:17][CH:18]=[CH:19][N:20]=2)[S:5][C:4]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([N:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[C:28](=[O:30])[CH3:29])[CH:22]=1)#[N:2].CN(C)C=O.[H-].[Na+].[F:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52]Br)=[CH:50][CH:49]=1>C(Cl)Cl.CCOC(C)=O>[C:1]([C:3]1[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[Cl:15])=[C:6]([C:16]2[N:17]([CH2:52][C:51]3[CH:54]=[CH:55][C:48]([F:47])=[CH:49][CH:50]=3)[CH:18]=[CH:19][N:20]=2)[S:5][C:4]=1[C:21]1[CH:26]=[CH:25][N:24]=[C:23]([N:27]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[C:28](=[O:30])[CH3:29])[CH:22]=1)#[N:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 58094958HCID 58094958, compound

Product 1

HCID 58095257HCID 58095257, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To the solution of N-{4-[3-cyano-4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)-2-thienyl]pyridin-2-yl}-N-(4-methoxybenzyl)acetamide (60.0 mg, 0.104 mmol) in dry N,N-Dimethylformamide (5.0 mL, 64 mmol) was added Sodium hydride (3.96 mg, 0.157 mmol). The resulted red-brown solution was stirred at r.t. for 10 min. 4-Fluorobenzyl bromide (32.6 mg, 0.172 mmol) was added and the mixture was stirred at r.t. for 2 hours, The mixture was quenched with aqueous saturated NaHCO3 (10 mL), diluted with water, extracted with DCM (4×25 mL), washed with water, brine, dried over Na2SO4, filtered, rotovaped to give a crude residue. Chromatograph in silica column using DCM/EtOAc (30/70 to 0/100) afforded a solid product (0.055 g, yield 77.1%). LCMS: (AA) ES+, 682, 684. 1H NMR (400 MHz, d1-chloroform) δ: 8.60-8.62 (d, J=5.02 Hz, 1H), 7.63 (s, br, 1H), 7.51-7.53 (m, 1H), 7.34 (m, 1H), 7.14-7.26 (m, 5H), 6.92-6.97 (m, 2H), 6.80-6.86 (m, 3H), 6.70-6.73 (m, 2H), 5.14 (m, 2H), 4.71-4.84 (m, 2H), 3.76 (s, 3H), 2.19 (s, 3H).

Workup

  1. stirringthe mixture was stirred at r.t. for 2 hours
  2. customThe mixture was quenched with aqueous saturated NaHCO3 (10 mL)
  3. additiondiluted with water
  4. extractionextracted with DCM (4×25 mL)
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customto give a crude residue

Sources & evidence

ORD record
ord-08624131faaf4586bb91fc03a21942eb
Source dataset
uspto-grants-2014_08
Patent number
US08796314B2

Reaction notes

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