Triethylamine → N-{5-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carbonyl}-methanesulfonamide

HRID 1792882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1792882
CCN=C=NCCCN(C)C.[C:12]([C:14]1[CH:19]=[CH:18][C:17]([C@H:20]2[C@:24]3([N:28]([CH3:29])[C:27](=[O:30])[N:26]([C:31]4[CH:36]=[C:35]([Cl:37])[CH:34]=[C:33]([Cl:38])[CH:32]=4)[C:25]3=[O:39])[CH2:23][N:22]([CH2:40][C:41]3[S:45][CH:44]=[C:43]([C:46]([OH:48])=O)[CH:42]=3)[CH2:21]2)=[CH:16][CH:15]=1)#[N:13].[CH3:49][S:50]([NH2:53])(=[O:52])=[O:51].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([C@H:20]2[C@:24]3([N:28]([CH3:29])[C:27](=[O:30])[N:26]([C:31]4[CH:32]=[C:33]([Cl:38])[CH:34]=[C:35]([Cl:37])[CH:36]=4)[C:25]3=[O:39])[CH2:23][N:22]([CH2:40][C:41]3[S:45][CH:44]=[C:43]([C:46]([NH:53][S:50]([CH3:49])(=[O:52])=[O:51])=[O:48])[CH:42]=3)[CH2:21]2)=[CH:18][CH:19]=1)#[N:13]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 72879MethanesulfonamideHCID 11635371Bms-587101

Produkt 1

HCID 60054871N-{5-[(5S*,9R*)-9-(4-Cyanophenyl)-3-(3,5-dichlorophenyl)-1-methyl-2,4-dioxo-1,3,7-triazaspiro[4.4]non-7-ylmethyl]-thiophene-3-carbonyl}-methanesulfonamideAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

EDCI (84 mg, 0.44 mmol) was added to a solution of Example 37 (100 mg, 0.18 mmol), methanesulfonamide (38 mg, 0.38 mmol), triethylamine (62 μl, 0.43 mmol) and a trace of DMAP in DCM (5 ml) at room temperature. After 48 h, water was added and the mixture was acidified by bubbling SO2. The organic layer was separated and the aqueous layer extracted twice with DCM. The combined organic layers were washed with brine and concentrated in vacuo. The resulting product was chromatographed over silica gel to yield the above-titled compound (38.9 mg) as an amorphous solid along with 55.6 mg of unreacted starting material. 1H NMR (CDCl3) δ 8.04 (1H, s), 7.62 (2H, d, J=8 Hz), 7.40 (1H, s), 7.25–7.3 (3H, m), 6.65 (2H, d, J=1.5 Hz), 3.8–4.1 (3H, m), 3.86 (3H, s), 3.3–3.4 (2H, m), 3.3.25 (3H, s), 3.15–3.3 (1H, m), 3.01 (1H, d, J=11 Hz).

Aufarbeitung

  1. customat room temperature
  2. customby bubbling SO2
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted twice with DCM
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated in vacuo
  7. customThe resulting product was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0c8cc087949049a8ae08d344d04c36da
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07078420B2

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