Diisopropylethylamine → HCID 58790370, Verbindung

HRID 418620

Reaktionsgleichung

Reaktionsgleichung von HRID 418620
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][C:4](O)=[O:5].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[Cl:29][CH2:30][CH2:31][N:32]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[S:49][C:48]3[C:43](=[N:44][CH:45]=[CH:46][C:47]=3[O:50][C:51]3[CH:56]=[CH:55][C:54]([NH2:57])=[CH:53][C:52]=3[F:58])[CH:42]=2)=[CH:37][CH:36]=1)[CH3:33].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:29][CH2:30][CH2:31][N:32]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:41]2[S:49][C:48]3[C:43](=[N:44][CH:45]=[CH:46][C:47]=3[O:50][C:51]3[CH:56]=[CH:55][C:54]([NH:57][C:4](=[O:5])[CH2:3][C:2]([NH:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)=[O:1])=[CH:53][C:52]=3[F:58])[CH:42]=2)=[CH:39][CH:40]=1)[CH3:33]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 2565932-(Phenylcarbamoyl)acetic acidHCID 587901534-(2-(4-(((2-Chloroethyl)(methyl)amino)methyl)phenyl)thieno[3,2-b]pyridin-7-yloxy)-3-fluorobenzenamine

Produkt 1

HCID 58790370HCID 58790370, VerbindungAusbeute 21,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of the acid 1 (142 mg, 2 eq, 1.58 mmol) in dry DCM (10 ml), at 0° C., was added, BOPCl (502 mg, 2 eq, 0.826 mmol) and the reaction mixture was stirred for 10 minutes. A solution of the amine 87 (348 mg, 0.79 mmol) and iPr2NEt (610 mg, 6 eq, 4.72 mmol) in dry DCM (7 ml) was then added and the reaction mixture was stirred at RT overnight. The reaction mixture was concentrated to dryness and partitioned between EtOAc and satd NaHCO3 soln, the organic phase was washed twice with saturated NaHCO3 then collected, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was purified by column chromatography (EtOAc) to afford the desired product 88 as an off-white solid (102 mg, 21% yield). 1H NMR (DMSO-d6) δ (ppm): 10.58 (s, 1H), 10.22 (s, 1H), 8.48 (d, J=5.28 Hz, 1H), 8.03 (s, 1H), 7.85 (m, 3H), 7.59 (m, 2H), 7.43 (m, 4H), 7.32 (m, 2H), 7.05 (t, J=7.43 Hz, 1H), 6.61 (m, 1H), 3.70 (t, J=6.65 Hz, 2H), 3.59 (s, 2H), 3.50 (s, 2H), 2.69 (m, 2H), 2.20 (s, 3H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc
  3. washthe organic phase was washed twice with saturated NaHCO3
  4. customthen collected
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure
  8. customthe crude was purified by column chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-a69aefa54ee04f29984f45fe93d62569
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093264B2

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