Diisopropylethylamine → HCID 89599450, compound

HRID 1406686Notes

Reaction equation

HRID 1406686 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[N:21]2[CH:22]=[C:23]([O:26][C@@H:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[C@@H:30]([NH2:37])[CH2:29][CH2:28]3)[CH:24]=[CH:25][C:20]2=[N:19][N:18]=1.CCN(C(C)C)C(C)C.[C:47]([C:51]1[CH:55]=[C:54]([NH:56][C:57](=O)[O:58]CC(Cl)(Cl)Cl)[N:53]([C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)[N:52]=1)([CH3:50])([CH3:49])[CH3:48]>O1CCOCC1>[C:47]([C:51]1[CH:55]=[C:54]([NH:56][C:57]([NH:37][C@@H:30]2[C:31]3[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=3)[C@@H:27]([O:26][C:23]3[CH:24]=[CH:25][C:20]4[N:21]([C:17]([C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=5[S:10][CH2:9][CH2:8][O:7][CH:2]5[CH2:3][CH2:4][CH2:5][CH2:6][O:1]5)=[N:18][N:19]=4)[CH:22]=3)[CH2:28][CH2:29]2)=[O:58])[N:53]([C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)[N:52]=1)([CH3:50])([CH3:48])[CH3:49]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 89599243HCID 89599243, compound

Product 1

HCID 89599450HCID 89599450, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 20 step b (60 mg, 0.11 mmol), DIPEA (26 μL, 0.15 mmol) and 2,2,2-trichloroethyl 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-ylcarbamate (56 mg, 0.138 mmol) in dioxane (5 mL) was heated at 80° C. for 20 h. The reaction was allowed to cool to RT, partitioned between H2O-DCM, the organic phase dried (MgSO4) and concentrated in vacuo. The residue was purified by FCC using MeOH in DCM (0 to 5%) to give the title compound as a yellow foam (38 mg, 45%). LCMS (Method 3): Rt 4.09 min, m/z 772 [MH+].

Workup

  1. custompartitioned between H2O-DCM
  2. dry with materialthe organic phase dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-d114053f94aa47368a15e88ef6fed62a
Source dataset
uspto-grants-2014_12
Patent number
US08916708B2

Reaction notes

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