Hydrochloric Acid → HCID 86641616, compound

HRID 1685200Notes

Reaction equation

HRID 1685200 reaction equation
[CH2:1]([CH:3]1[C:11]2[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[N:19]([CH2:34][C@@H:35]5[CH2:40][CH2:39][CH2:38][CH2:37][N:36]5C(OCC5C=CC=CC=5)=O)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=5)[N:22]=4)[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[NH:5][C:4]1=[O:51])[CH3:2].[ClH:52]>>[ClH:52].[ClH:52].[ClH:52].[CH2:1]([CH:3]1[C:11]2[C:10]([N:12]3[CH2:17][CH2:16][CH:15]([C:18]4[N:19]([CH2:34][C@@H:35]5[CH2:40][CH2:39][CH2:38][CH2:37][NH:36]5)[CH:20]=[C:21]([C:23]5[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:32])([F:31])[F:33])[CH:24]=5)[N:22]=4)[CH2:14][CH2:13]3)=[N:9][CH:8]=[N:7][C:6]=2[NH:5][C:4]1=[O:51])[CH3:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 59322423HCID 59322423, compound

Product 1

HCID 86641616HCID 86641616, compoundYield 90%

Conditions

Temperature
50 °C

Procedure

Charge (2S)-benzyl 2-((2-(1-(5-ethyl-6-oxo-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-yl)-4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-1-yl)methyl)piperidine-1-carboxylate (0.45 g; 1.0 eq) in concentrated HCl (10 mL) and heat at 50° C. for 1 hour. After completion, concentrate the reaction mass, strip with toluene and triturate and wash with diethyl ether followed by DCM and pentane. Dry under vacuum to get 0.39 g (90%) of the title compound as an off-white solid. (ES+): m/z=572 (M+H).

Workup

  1. concentrationAfter completion, concentrate the reaction mass, strip with toluene
  2. customtriturate
  3. washwash with diethyl ether
  4. customDry under vacuum

Sources & evidence

ORD record
ord-2f8724043c6845c78fc727013186ad43
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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