Diisopropylethylamine → HCID 57863462, compound

HRID 1446727Notes

Reaction equation

HRID 1446727 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][N:9]3[C:12]([C:15]4[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=4)=[CH:13][N:14]=[C:8]3[CH:7]=2)=[CH:2]1.ClC(Cl)(Cl)C[O:26][C:27](=O)[NH:28][C:29]1[N:30]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:33]=1.C(N(C(C)C)CC)(C)C>CS(C)=O>[C:34]([C:32]1[CH:33]=[C:29]([NH:28][C:27]([NH:20][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([C:12]3[N:9]4[CH:10]=[CH:11][C:6]([C:3]5[CH:4]=[CH:5][S:1][CH:2]=5)=[CH:7][C:8]4=[N:14][CH:13]=3)=[CH:16][CH:17]=2)=[O:26])[N:30]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:31]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 68546834HCID 68546834, compound

Product 1

HCID 57863462HCID 57863462, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
62 °C

Procedure

Dissolve 4-(7-thien-3-yl-imidazo[1,2-a]pyridin-3-yl)-benzylamine (0.058 g, 0.19 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.093 g, 0.23 mmol) and diisopropylethylamine (0.071 g, 0.55 mmol) in DMSO (3.6 mL). Heat the mixture at 62° C. for 8 hours. After evaporation of solvent, dilute the reaction with water and ethyl acetate. Extract the water phase with ethyl acetate and wash the combined organic layers with saturated aqueous saturated sodium chloride and evaporate to dryness. Purify the residue by silica gel column chromatography (dichlromethane/ethyl acetate gradient) to give 0.023 g (21% yield) of desired compound: MS(ES), m/z 561 (M+1).

Workup

  1. customAfter evaporation of solvent
  2. additiondilute
  3. customthe reaction with water and ethyl acetate
  4. extractionExtract the water phase with ethyl acetate
  5. washwash the combined organic layers with saturated aqueous saturated sodium chloride
  6. customevaporate to dryness
  7. customPurify the residue by silica gel column chromatography (dichlromethane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-10e4639574a04152a2f304cc2e907763
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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