Diisopropylethylamine → HCID 59322424, compound

HRID 1685209Notes

Reaction equation

HRID 1685209 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[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[N:31]([CH3:39])[C:32](=[O:38])[NH:33]2.C[CH2:41][N:42](C(C)C)[CH:43](C)C>CN1C(=O)CCC1>[F:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:22]3[CH2:23][CH2:24][N:25]([C:29]4[N:37]=[CH:36][N:35]=[C:34]5[C:30]=4[N:31]([CH3:39])[C:32](=[O:38])[NH:33]5)[CH2:26][CH2:27]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

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 14518099HCID 14518099, compoundHCID 67264706HCID 67264706, compound

Product 1

HCID 59322424HCID 59322424, compoundYield 9.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Combine 2-(4-(3,4-difluorophenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl-N,N-dimethyl ethanamine 3HCl (0.3 g; 0.00068 mol), 6-chloro-7-methyl-7,9-dihydro-purin-8-one (0.15 g; 0.00081 mol), DIPEA (1.07 mL; 0.0062 mol) in NMP (9 mL) and stir at 150° C. in microwave for 45 min. Cool, and quench the reaction with saturated sodium bicarbonate solution and extract with EA. Evaporate the EA layer and purify on silica gel using DCM and methanol as eluent to give the title compound (0.032 g; 9.3%). MS (ES+): m/z=484 (M+1).

Workup

  1. temperatureCool
  2. customquench
  3. customthe reaction with saturated sodium bicarbonate solution
  4. extractionextract with EA
  5. customEvaporate the EA layer
  6. custompurify on silica gel

Sources & evidence

ORD record
ord-8599121dea23456988af40db8080f49c
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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