Diisopropylethylamine → HCID 86687120, compound

HRID 2285109Notes

Reaction equation

HRID 2285109 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([C:19]1[N:23]2[CH:24]=[C:25]([O:28][C@H:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@@H:32]([NH2:39])[CH2:31][CH2:30]3)[CH:26]=[CH:27][C:22]2=[N:21][N:20]=1)[CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11].ClC(Cl)(Cl)C[O:43][C:44](=O)[NH:45][C:46]1[N:47]([C:55]2[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][CH:56]=2)[N:48]=[C:49]([C:51]([CH3:54])([CH3:53])[CH3:52])[CH:50]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[C:51]([C:49]1[CH:50]=[C:46]([NH:45][C:44]([NH:39][C@@H:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[C@H:29]([O:28][C:25]3[CH:26]=[CH:27][C:22]4[N:23]([C:19]([C@:3]5([CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:14])[CH3:15])[CH:10]([CH3:11])[CH3:12])[CH2:4][CH2:5][CH2:6][N:2]5[CH3:1])=[N:20][N:21]=4)[CH:24]=3)[CH2:30][CH2:31]2)=[O:43])[N:47]([C:55]2[CH:60]=[CH:59][C:58]([CH3:61])=[CH:57][CH:56]=2)[N:48]=1)([CH3:54])([CH3:52])[CH3:53]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 89624153HCID 89624153, compound

Product 1

HCID 86687120HCID 86687120, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Intermediate 85j (230 mg, 0.418 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. which is incorporated herein by reference in its entirety; 253 mg, 0.628 mmol) and DIPEA (215 mg, 1.67 mmol) in DMF (4 mL) was stirred at 50° C. for 1 h. The mixture was diluted with EtOAc, washed with water (2×), brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound as a white foam (250 mg, 48%). LCMS (Method 3): Rt 3.70 min, m/z 805 [MH+].

Workup

  1. washwashed with water (2×), brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-989dc586009f436c816a8c74b1bc0e5c
Source dataset
uspto-grants-2015_09
Patent number
US09145413B2

Reaction notes

Loading…