Triethylamine → Top-1288

HRID 1423257Notes

Reaction equation

HRID 1423257 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:11]=2[O:25][CH3:26])C=CC=CC=1.[NH2:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]([O:39][C:40]2[CH:45]=[CH:44][N:43]=[C:42]([NH:46][C:47]3[CH:48]=[C:49]([CH:63]=[C:64]([C:66]#[CH:67])[CH:65]=3)[C:50]([NH:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH3:62])=[O:51])[N:41]=2)=[CH:31][CH:30]=1.CCN(CC)CC>C(OC(C)=O)(C)C>[C:16]([C:14]1[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:11]([O:25][CH3:26])=[C:10]([NH:9][C:8](=[O:27])[NH:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]([O:39][C:40]3[CH:45]=[CH:44][N:43]=[C:42]([NH:46][C:47]4[CH:48]=[C:49]([CH:63]=[C:64]([C:66]#[CH:67])[CH:65]=4)[C:50]([NH:52][CH2:53][CH2:54][O:55][CH2:56][CH2:57][O:58][CH2:59][CH2:60][O:61][CH3:62])=[O:51])[N:41]=3)=[CH:31][CH:30]=2)[CH:15]=1)([CH3:18])([CH3:19])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86275692Phenyl 5-tert-butyl-2-methoxy-3-(methylsulfonamido)phenylcarbamateHCID 117598555HCID 117598555, compound

Product 1

HCID 81689783Top-1288

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

A stirred mixture of phenyl(5-(tert-butyl)-2-methoxy-3-(methylsulfonamido)phenyl)-carbamate (see step 1(vii) above; 95 mg, 0.239 mmol), the product from step (vi) above (120 mg, 0.217 mmol) and Et3N (6 μL, 0.043 mmol) in i-PrOAc (3 mL) was heated at 70° C. overnight. The reaction was cooled to rt and concentrated in vacuo. The remainder was purified by chromatography on silica gel (40 g column, 0-5% MeOH in EtOAc) to afford an oil, which was triturated with diethyl ether to afford a light beige solid. The crude product was purified by preparative HPLC (Varian, Basic (10 mM Ammonium Bicarbonate), Waters X-Bridge Prep-C18, 5 μm, 19×50 mm column, 35-70% MeCN in Water) to afford the title compound (69 mg) as an off-white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe remainder was purified by chromatography on silica gel (40 g column, 0-5% MeOH in EtOAc)
  3. customto afford an oil, which
  4. customwas triturated with diethyl ether
  5. customto afford a light beige solid
  6. customThe crude product was purified by preparative HPLC (Varian, Basic (10 mM Ammonium Bicarbonate), Waters X-Bridge Prep-C18, 5 μm, 19×50 mm column, 35-70% MeCN in Water)

Sources & evidence

ORD record
ord-031175c58c3b4c999e169d65f27e31f5
Source dataset
uspto-grants-2015_01
Patent number
US08927563B2

Reaction notes

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