Diisopropylethylamine → HCID 178525121, compound

HRID 2283947Notes

Reaction equation

HRID 2283947 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[NH:12][CH:13]=2)=[CH:5][C:4]=1[C:20]([F:23])([F:22])[F:21].C(N(C(C)C)C(C)C)C.[CH2:33]([O:40][C:41](ON1C(=O)CCC1=O)=[O:42])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:41]([O:40][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:42])[CH2:16][CH2:15]3)[NH:12][CH:13]=2)=[CH:5][C:4]=1[C:20]([F:21])([F:22])[F:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83172Benzyl succinimido carbonateHCID 178478946HCID 178478946, compound

Product 1

HCID 178525121HCID 178525121, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 4-(4-(4-fluoro-3-(trifluoromethyl)phenyl)-1H-imidazol-2-yl)piperidine hydrochloride salt (1510.00 mg; 3.91 mmol; 1.00 eq.) in DCM was added Ethyldiisopropylamine (2.81 ml; 15.64 mmol; 4.00 eq.) and stirred for 5 mins. N-(Benzyloxycarbonyloxy) succinimide (1169.26 mg; 4.69 mmol; 1.20 eq.) was then added. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with DCM, washed with water, 5% NaHCO3 aq and brine. The organic layer was dried and concentrated. The residue was subjected to SNAP column (100 g), eluted with 20-80% EA in hexane to afford the title compound (1310 mg, yield 74.9%).

Workup

  1. stirringThe reaction mixture was stirred at RT overnight
  2. washwashed with water, 5% NaHCO3 aq and brine
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. washeluted with 20-80% EA in hexane

Sources & evidence

ORD record
ord-f82e324a24164e91ad726f8ce1bc6158
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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