Methyl 3-formylbenzoate → 3-[(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-methyl]-benzoic acid methyl ester

HRID 1819481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1819481
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][C:28]([F:31])([F:30])[F:29])[N:11]=2)[CH2:4][CH2:3]1.[CH3:32][O:33][C:34](=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH:41]=O)[CH:36]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:32][O:33][C:34](=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([CH2:41][NH:1][CH:2]2[CH2:3][CH2:4][CH:5]([CH2:8][NH:9][C:10]3[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][N:13]=[C:12]([NH:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][C:28]([F:30])([F:31])[F:29])[N:11]=3)[CH2:6][CH2:7]2)[CH:36]=1

Komponenten

5

Edukt 3

HCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 16202211N4-(4-amino-cyclohexylmethyl)-5-nitro-N2-(2-trifluoromethoxy-benzyl)-pyrimidine-2,4-diamine

Produkt 1

HCID 598456853-[(4-{[5-Nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-methyl]-benzoic acid methyl esterAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of N4-(4-amino-cyclohexylmethyl)-5-nitro-N2-(2-trifluoromethoxy-benzyl)-pyrimidine-2,4-diamine (100 mg, 0.23 mmol) and 3-formyl-benzoic acid methyl ester (41 mg, 0.25 mmol) in DCM (1 mL) was added sodium triacetoxyborohydride (58 mg, 0.27 mmol). The mixture was stirred at room temperature for 18 h then quenched with excess water. The mixture was diluted with DCM and the organic layer separated and dried over Na2SO4. The solvent was removed in vacuo and the residue purified by column chromatography using an ISCO combi-flash cartridge (silica gel, DCM/MeOH) to afford 3-[(4-{[5-nitro-2-(2-trifluoromethoxy-benzylamino)-pyrimidin-4-ylamino]-methyl}-cyclohexylamino)-methyl]-benzoic acid methyl ester (76 mg, 57%), m/z 589 (M+1)+.

Aufarbeitung

  1. customthen quenched with excess water
  2. additionThe mixture was diluted with DCM
  3. customthe organic layer separated
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff43e96a68de4006b5ad90744b4459e2
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601714B2

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