Dimethylformamide → HCID 59322416, compound

HRID 1685204Notes

Reaction equation

HRID 1685204 reaction equation
Cl.Cl.Cl.[F:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]([CH:17](N(C)C)[CH3:18])[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11].Cl[C:29]1[C:30]2[C:37]([CH3:39])([CH3:38])[C:36](=[O:40])[NH:35][C:31]=2[N:32]=[CH:33][N:34]=1.[CH3:41][N:42](C=O)[CH3:43]>>[F:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:22]3[CH2:27][CH2:26][N:25]([C:29]4[C:30]5[C:37]([CH3:39])([CH3:38])[C:36](=[O:40])[NH:35][C:31]=5[N:32]=[CH:33][N:34]=4)[CH2:24][CH2:23]3)[N:15]([CH2:17][CH2:18][N:42]([CH3:43])[CH3:41])[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 67264706HCID 67264706, compoundHCID 86641620HCID 86641620, compound

Product 1

HCID 59322416HCID 59322416, compoundYield 15.92%

Procedure

Combine 2-(4-(3,4-difluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl-N,N-dimethyl ethanamine tris hydrochloride (0.28 g; 0.00064 mol), 4-chloro-5,5-dimethyl-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.15 g; 0.00076 mol), TEA (0.74 mL; 0.0053 mol) in DMF (8.43 mL) and heat in microwave at 150° C. for 3 h; cool to RT and evaporate under vacuum. Quench the reaction with saturated sodium bicarbonate solution and extract with EA. Evaporate the EA layer and purify on silica column (60-120 mesh) packed in DCM, first with two volumes of 10% Acetone/DCM followed by 1-5% MeOH/DCM as eluent to give the title compound (0.05 g; 15.92%). MS (ES+): m/z=496 (M+H).

Workup

  1. customevaporate under vacuum
  2. customQuench
  3. customthe reaction with saturated sodium bicarbonate solution
  4. extractionextract with EA
  5. customEvaporate the EA layer
  6. custompurify on silica column (60-120 mesh)

Sources & evidence

ORD record
ord-edb434c59e144115a2c44623329d8bfc
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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