Diisopropylethylamine → HCID 89623869, compound

HRID 1402267Notes

Reaction equation

HRID 1402267 reaction equation
[CH:1]([Si:4]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[O:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]1[N:18]2[CH:19]=[C:20]([O:23][C@H:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C@@H:27]([NH2:34])[CH2:26][CH2:25]3)[CH:21]=[CH:22][C:17]2=[N:16][N:15]=1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.ClC(Cl)(Cl)C[O:53][C:54](=O)[NH:55][C:56]1[N:57]([C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)[N:58]=[C:59]([C:61]([CH3:64])([CH3:63])[CH3:62])[CH:60]=1>O1CCOCC1>[C:61]([C:59]1[CH:60]=[C:56]([NH:55][C:54]([NH:34][C@@H:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:24]([O:23][C:20]3[CH:21]=[CH:22][C:17]4[N:18]([C:14]([C@@H:10]5[CH2:11][CH2:12][CH2:13][N:9]5[CH2:8][CH2:7][CH2:6][O:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:35]([CH3:37])[CH3:36])[CH:38]([CH3:40])[CH3:39])=[N:15][N:16]=4)[CH:19]=3)[CH2:25][CH2:26]2)=[O:53])[N:57]([C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)[N:58]=1)([CH3:64])([CH3:62])[CH3:63]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamate2×HCID 86687112HCID 86687112, compound

Product 1

HCID 89623869HCID 89623869, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of Intermediate 84g (140 mg, 0.25 mmol) in 1,4-dioxane (3.00 mL) was added DIPEA (86.0 μL, 0.50 mmol) and (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Synthetic Communications, 2009, 39, 3999-4009, which is incorporated herein by reference in its entirety; 100 mg, 0.25 mmol). The reaction was heated to 60° C. overnight then further (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (50.0 mg, 0.12 mmol) was added and heating at 60° C. continued overnight. The reaction was cooled and partitioned between EtOAc and water. The aqueous layer was then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound (70.0 mg, 34%). LCMS (Method 1): Rt 3.46, m/z 820.4 [MH+].

Workup

  1. temperatureheating at 60° C.
  2. temperatureThe reaction was cooled
  3. custompartitioned between EtOAc and water
  4. extractionThe aqueous layer was then extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-7162e8c5cc1a4fb4b39eeba9ff06dd93
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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