Diisopropylethylamine → HCID 123647418, compound

HRID 2200038Notes

Reaction equation

HRID 2200038 reaction equation
ClC(Cl)(Cl)CO[C:5](=[O:17])[NH:6][C:7]1[N:8]([CH3:16])[N:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1.[CH:20]([Si:23]([CH:56]([CH3:58])[CH3:57])([CH:53]([CH3:55])[CH3:54])[O:24][CH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]2[N:36]3[CH:37]=[C:38]([O:41][C@H:42]4[C:51]5[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=5)[C@@H:45]([NH2:52])[CH2:44][CH2:43]4)[CH:39]=[CH:40][C:35]3=[N:34][N:33]=2)[CH2:28][CH2:27]1)([CH3:22])[CH3:21].CCN(C(C)C)C(C)C>O1CCOCC1.C(Cl)Cl>[C:12]([C:10]1[CH:11]=[C:7]([NH:6][C:5]([NH:52][C@@H:45]2[C:46]3[C:51](=[CH:50][CH:49]=[CH:48][CH:47]=3)[C@H:42]([O:41][C:38]3[CH:39]=[CH:40][C:35]4[N:36]([C:32]([N:29]5[CH2:28][CH2:27][CH:26]([CH2:25][O:24][Si:23]([CH:20]([CH3:22])[CH3:21])([CH:56]([CH3:58])[CH3:57])[CH:53]([CH3:55])[CH3:54])[CH2:31][CH2:30]5)=[N:33][N:34]=4)[CH:37]=3)[CH2:43][CH2:44]2)=[O:17])[N:8]([CH3:16])[N:9]=1)([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 594208722,2,2-Trichloroethyl (3-tert-butyl-1-methyl-1H-pyrazol-5-yl)carbamateHCID 86687046HCID 86687046, compound

Product 1

HCID 123647418HCID 123647418, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of (5-tert-butyl-2-methyl-2H-pyrazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (US 20040192653, 90 mg, 0.273 mmol), Intermediate 14e (150 mg, 0.273 mmol) and DIPEA (71 μL, 0.409 mmol) in dioxane (2 mL) was heated at 60° C. for 48 h. The reaction mixture was cooled and diluted with DCM (5 mL). The organic layer was washed with water (3×5 mL), passed through a phase separator and concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to afford the title compound (117 mg, 59%). LCMS (Method 3): Rt: 5.12 min, m/z 729 [MH+].

Workup

  1. temperatureThe reaction mixture was cooled
  2. washThe organic layer was washed with water (3×5 mL)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-e0db0c0fec2f4a0f9dc5570fc3d7a83b
Source dataset
uspto-grants-2016_06
Patent number
US09359354B2

Reaction notes

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