Diisopropylethylamine → HCID 59322460, compound

HRID 1685207Notes

Reaction equation

HRID 1685207 reaction equation
Cl.Cl.Cl.[F:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11].Cl[C:31]1[C:32]2[CH2:39][C:38](=[O:40])[NH:37][C:33]=2[N:34]=[CH:35][N:36]=1.CCN(C(C)C)C(C)C>CC(O)C>[F:4][C:5]1[CH:6]=[C:7]([C:12]2[N:13]=[C:14]([CH:24]3[CH2:25][CH2:26][N:27]([C:31]4[C:32]5[CH2:39][C:38](=[O:40])[NH:37][C:33]=5[N:34]=[CH:35][N:36]=4)[CH2:28][CH2:29]3)[N:15]([CH2:17][CH2:18][N:19]3[CH2:20][CH2:21][CH2:22][CH2:23]3)[CH:16]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 120958704-chloro-5H,6H,7H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 67264903HCID 67264903, compound

Product 1

HCID 59322460HCID 59322460, compoundYield 15.67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Combine 4-(4-(3,4-difluoro-phenyl)-1-(2-pyrrolidin-1-yl-ethyl)-1H-imidazol-2-yl)-piperidine tris hydrochloride (0.3 g; 0.00065 mol), 4-chloro-5,7-dihydro-pyrrolo[2,3-d]pyrimidin-6-one (0.15 g; 0.00083 mol), DIPEA, (1.00 mL, 0.0057 mol) into IPA (9 mL) and heat in a microwave at 80° C. for 1 h; cool and concentrate. Quench with saturated sodium bicarbonate solution and extract with EA. Evaporate the EA and purify by column chromatography using 0-10% MeOH/DCM as eluent to give the title compound (0.05 g; 15.67%). MS (ES+): m/z=494 (M+1).

Workup

  1. temperaturecool
  2. concentrationconcentrate
  3. customQuench with saturated sodium bicarbonate solution
  4. extractionextract with EA
  5. customEvaporate the EA
  6. custompurify by column chromatography

Sources & evidence

ORD record
ord-266b970d7d7244479dd31dd72bfcac77
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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