Diisopropylethylamine → HCID 86687092, compound

HRID 1402238Notes

Reaction equation

HRID 1402238 reaction equation
[N:1]1([C:6]2[N:10]3[CH:11]=[C:12]([O:15][C@H:16]4[C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[C@@H:19]([NH2:26])[CH2:18][CH2:17]4)[CH:13]=[CH:14][C:9]3=[N:8][N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC(Cl)(Cl)C[O:30][C:31](=O)[NH:32][C:33]1[N:34]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:35]=[C:36]([C:38]([CH3:41])([CH3:40])[CH3:39])[CH:37]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[C:38]([C:36]1[CH:37]=[C:33]([NH:32][C:31]([NH:26][C@@H:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:16]([O:15][C:12]3[CH:13]=[CH:14][C:9]4[N:10]([C:6]([N:1]5[CH2:5][CH2:4][CH2:3][CH2:2]5)=[N:7][N:8]=4)[CH:11]=3)[CH2:17][CH2:18]2)=[O:30])[N:34]([C:42]2[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=2)[N:35]=1)([CH3:41])([CH3:39])[CH3:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 86687091HCID 86687091, compound

Product 1

HCID 86687092HCID 86687092, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of Intermediate 75b (62.0 mg, 0.18 mmol), (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (Synthetic Communications, 2009, 39, 3999-4009; 78.9 mg, 0.195 mmol), DIPEA (46.3 μL, 0.27 mmol) and 1,4-dioxane (2.5 mL) were heated to 60° C. for 18 h. After cooling the solvent was evaporated in vacuo. The residue was purified by FCC, using 0-10% MeOH in DCM, then further purified by HPLC (30-98% MeCN in H2O, 0.1% HCO2H) to give the title compound as an off-white solid (22 mg, 20%). LCMS (Method 5) Rt 4.30 min, m/z 605 [MH+]. 1H NMR (400 MHz, d6-DMSO): 1.27 (9H, s), 1.79-2.15 (8H, m), 2.36 (3H, s), 3.49 (4H, m), 4.81 (1H, m), 5.51 (1H, t, J 4.5), 6.30 (1H, s), 7.03 (1H, dd, J 10.1, 2.2), 7.09 (1H, d, J 8.5), 7.25-7.40 (8H, m), 7.51 (1H, m), 7.83 (1H, m), 8.07 (1H, s).

Workup

  1. temperatureAfter cooling the solvent
  2. customwas evaporated in vacuo
  3. customThe residue was purified by FCC
  4. customfurther purified by HPLC (30-98% MeCN in H2O, 0.1% HCO2H)

Sources & evidence

ORD record
ord-f39adf0def6d46c185935f7c5544f508
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…