1,2-Dichloroethane → 5-(2,4-Dichlorophenyl)-7-methyl-2-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazo[1,2-a]pyrimidine-6-carbonitrile

HRID 1868486Notes

Reaction equation

HRID 1868486 reaction equation
[C:1]([C:3]1[C:4]([CH3:24])=[N:5][C:6]2[N:7]([CH:17]=[C:18]([CH2:20][C:21](O)=[O:22])[N:19]=2)[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])#[N:2].[CH:25]1[CH:30]=[N:29][C:28]2N(O)N=N[C:27]=2C=1.C(Cl)CCl.N1CCCC1>CC#N>[Cl:16][C:10]1[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=1[C:8]1[N:7]2[CH:17]=[C:18]([CH2:20][C:21](=[O:22])[N:29]3[CH2:28][CH2:27][CH2:25][CH2:30]3)[N:19]=[C:6]2[N:5]=[C:4]([CH3:24])[C:3]=1[C:1]#[N:2]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 31268Pyrrolidine2×HCID 181649HOAtHCID 579824512-(6-Cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetic acid

Product 1

HCID 579824525-(2,4-Dichlorophenyl)-7-methyl-2-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazo[1,2-a]pyrimidine-6-carbonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(6-cyano-5-(2,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyrimidin-2-yl)acetic acid (72 mg, 0.2 mmol) in CH3CN (0.7 mL) were added HOAT (41 mg, 0.3 mmol) and EDC (77 mg, 0.4 mmol). After one min all of the solids had dissolved to produce a clear tan to brown solution. At 5 min, pyrrolidine (14.5 mg, 0.2 mmol) was added. At 20 min from the addition of pyrrolidine, the reaction was quenched with EtOAc (3 mL) and then washed with satd aq NaHCO3 (2×3 mL), satd aq NH4Cl (2×3 mL), and water (3 mL). The organic layer was dried with MgSO4, filtered, and concentrated to yield 5-(2,4-dichlorophenyl)-7-methyl-2-(2-oxo-2-(pyrrolidin-1-yl)ethyl)imidazo[1,2-a]pyrimidine-6-carbonitrile (46 mg, 56%) as a yellow-brown oil.

Workup

  1. dissolutionAfter one min all of the solids had dissolved
  2. customto produce a clear tan to brown solution
  3. customthe reaction was quenched with EtOAc (3 mL)
  4. washwashed with satd aq NaHCO3 (2×3 mL)
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-79fae576511e48178fed1ebfc7fd43cc
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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