Water → HCID 59322423, compound

HRID 1685198Notes

Reaction equation

HRID 1685198 reaction equation
Cl.Cl.Cl.[F:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)[N:14]([CH2:16][C@@H:17]3[CH2:22][CH2:21][CH2:20][CH2:19][N:18]3[C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH:15]=2)=[CH:7][C:6]=1[C:39]([F:42])([F:41])[F:40].CC[N:45]([CH:49]([CH3:51])C)[CH:46]([CH3:48])C.C[CH:53](O)[CH3:54].[OH2:56]>>[CH2:53]([CH:51]1[C:48]2[C:11]([N:36]3[CH2:37][CH2:38][CH:33]([C:13]4[N:14]([CH2:16][C@@H:17]5[CH2:22][CH2:21][CH2:20][CH2:19][N:18]5[C:23]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:24])[CH:15]=[C:11]([C:8]5[CH:9]=[CH:10][C:5]([F:4])=[C:6]([C:39]([F:42])([F:40])[F:41])[CH:7]=5)[N:12]=4)[CH2:34][CH2:35]3)=[N:12][CH:13]=[N:14][C:46]=2[NH:45][C:49]1=[O:56])[CH3:54]

Participants

5

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 81531DiisopropylethylamineHCID 86641613HCID 86641613, compound

Product 1

HCID 59322423HCID 59322423, compound

Procedure

Combine (S)-benzyl 2-((4-(4-fluoro-3-(trifluoromethyl)phenyl)-2-(piperidin-4-yl)-1H-imidazol-1-yl)methyl)piperidine-1-carboxylate trihydrochloride (1.1 g, 0.00168 mol, 1.0 eq); 4-chloro-5-ethyl-5,7-dihydro-pyrrolo[2,3d]pyrimidin-6-one (0.4 g, 0.002 mol, 1.2 eq); DIPEA (2 mL, 0.011 mol, 7.0 eq) and 2-propanol (20 mL) in a pressure tube and heat at 120° C. overnight under sealed condition. Cool the reaction mass and dilute with water. Extract in EA and wash the organic layer with brine. Dry over anhydrous sodium sulfate and concentrate the crude compound. Purify on silica gel (100-200 mesh) column using 10% acetone-DCM as eluent. Pool the fractions containing the desired compound and concentrate under vacuum to the title compound. MS (ES+): m/z=706 (M+H).

Workup

  1. customunder sealed condition
  2. temperatureCool the reaction mass
  3. extractionExtract in EA
  4. washwash the organic layer with brine
  5. dry with materialDry over anhydrous sodium sulfate
  6. concentrationconcentrate the crude compound
  7. customPurify on silica gel (100-200 mesh) column
  8. additionPool the fractions containing the desired compound
  9. concentrationconcentrate under vacuum to the title compound

Sources & evidence

ORD record
ord-4f5024d263e24b82a6590b256ff21f9a
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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