Acetaldehyde → 1-{3-[4-Amino-7-(1-ethyl-piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-phenyl}-3-(3,5-dichloro-phenyl)-urea

HRID 916788

Reaktionsgleichung

Reaktionsgleichung von HRID 916788
[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH:37](=O)[CH3:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.C1COCC1>[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:31]3[CH2:32][CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH2:36]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 672198621-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-urea

Produkt 1

HCID 672204331-{3-[4-Amino-7-(1-ethyl-piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-phenyl}-3-(3,5-dichloro-phenyl)-ureaAusbeute 10,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 1-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-urea (100 mg, 0.19 mmol) and acetaldehyde (8.4 mg, 0.19 mmol) in DMF/THF (20%, 10 mL) was stirred for 30 minutes at room temperature. Sodium triacetoxyborohydride (61 mg, 0.29 mmol) was added to the reaction mixture, stirred for 3.5 hours, and concentrated in vacuo. Purification by reverse phase preparative HPLC (HPLC method 2) provided the title compound as a white solid (11 mg, 10%). MS: 553.5 (MH+); HPLC Rf: 1.7 min. (HPLC method 2); HPLC purity: 100%.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customPurification by reverse phase preparative HPLC (HPLC method 2)

Quellen und Nachweise

ORD-Eintrag
ord-954eba2bdeda4fa7bcacefd67edd5c6b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07271262B2

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