Diisopropylethylamine → HCID 87279747, compound

HRID 2040220Notes

Reaction equation

HRID 2040220 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:51])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=4[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:21][CH2:20]3)=[CH:15][C:14]=2[O:41][C:42]2[CH:43]=[C:44]3[CH:50]=[CH:49][NH:48][C:45]3=[N:46][CH:47]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:52]([O-:54])=[O:53].[NH2:55][CH:56]1[CH2:61][CH2:60][N:59]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:58][CH2:57]1.CCN(C(C)C)C(C)C>O1CCOCC1.C(OCC)(=O)C>[NH:48]1[C:45]2=[N:46][CH:47]=[C:42]([O:41][C:14]3[CH:15]=[C:16]([N:19]4[CH2:20][CH2:21][N:22]([CH2:25][C:26]5[CH2:31][CH2:30][C:29]([CH3:32])([CH3:33])[CH2:28][C:27]=5[C:34]5[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=5)[CH2:23][CH2:24]4)[CH:17]=[CH:18][C:13]=3[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:55][CH:56]4[CH2:57][CH2:58][N:59]([C:62]([O:64][C:65]([CH3:68])([CH3:67])[CH3:66])=[O:63])[CH2:60][CH2:61]4)=[C:3]([N+:52]([O-:54])=[O:53])[CH:4]=3)(=[O:10])=[O:9])=[O:51])[CH:43]=[C:44]2[CH:50]=[CH:49]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 56591275HCID 56591275, compound

Product 1

HCID 87279747HCID 87279747, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of EXAMPLE 82 (800 mg) and tert-butyl 4-aminopiperidine-1-carboxylate (203 mg) in dioxane (10 mL) was added Hunig's Base (1 mL). The mixture was stirred at 120° C. overnight. The mixture was diluted with ethyl acetate (200 mL) and washed with water, brine and dried over Na2SO4. After filtration and evaporation of solvent, the residue was loaded on a silica gel cartridge and eluted with 3% methanol in dichloromethane to give the title compound.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and evaporation of solvent
  4. washeluted with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-07ff4febbe4140658eb0f9304dea6874
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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