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1,2-Dichloroethane → tert-butyl 4-(3-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)benzoyl)piperazine-1-carboxylate

HRID 1487166
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1487166
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:42])[C:12](=[O:41])[C:13]([CH3:40])=[C:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:16](=[O:30])[N:15]2[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([OH:36])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[N:57]1([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1.CCN(C(C)C)C(C)C>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:11]([CH3:42])[C:12](=[O:41])[C:13]([CH3:40])=[C:14]2[C:19]=1[C:18](=[O:20])[N:17]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:16](=[O:30])[N:15]2[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34]([N:60]1[CH2:59][CH2:58][N:57]([C:63]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])=[O:64])[CH2:62][CH2:61]1)=[O:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 898280673-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)benzoic acid

Produkt 1

HCID 89828068
tert-butyl 4-(3-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)benzoyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 3-(5-((2-fluoro-4-iodophenyl)amino)-3-(4-methoxybenzyl)-6,8-dimethyl-2,4,7-trioxo-3,4,6,7-tetrahydropyrido[4,3-d]pyrimidin-1(2H)-yl)benzoic acid (1 g, 1.465 mmol), EDC (0.421 g, 2.198 mmol), HOBT (0.337 g, 2.198 mmol) and tert-butyl piperazine-1-carboxylate (0.409 g, 2.198 mmol) in THF (5 ml); cooled to 0° C., was added Hunig's base (0.512 ml, 2.93 mmol). The resulting mixture was stirred under N2 atm for 2 h at room temperature. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (25 ml) and water (25 ml). The organic phase was separated and aq. phase was re-extracted with ethyl acetate. The combined organic layers were dried over sodium sulphate and evaporated in vacuo to obtain crude product, which was carried forward for the next step without further purification.

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate (25 ml) and water (25 ml)
  3. customThe organic phase was separated
  4. extractionaq. phase was re-extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over sodium sulphate
  6. customevaporated in vacuo
  7. customto obtain crude product, which
  8. customwas carried forward for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-699864b406394eb98d658766c3c4049f
Quelldatensatz
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09428499B2

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