Acetic Acid → HCID 178518684, 화합물

HRID 605009노트

반응식

HRID 605009 반응식
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[NH:11][N:10]=2)[CH2:5][CH2:4]1.[O:20]=[C:21]1[C:30]2[N:29]=[C:28]([C:31]3[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=3)[C:27]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[CH:26][C:25]=2[CH:24]=[CH:23][NH:22]1.C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN(C=O)C.CO>[C:39]1([C:27]2[C:28]([C:31]3[CH:32]=[CH:33][C:34]([CH2:35][N:3]4[CH2:8][CH2:7][CH:6]([C:9]5[N:13]=[C:12]([C:14]6[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=6)[NH:11][N:10]=5)[CH2:5][CH2:4]4)=[CH:37][CH:38]=3)=[N:29][C:30]3[C:21](=[O:20])[NH:22][CH:23]=[CH:24][C:25]=3[CH:26]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 59846152HCID 59846152, 화합물HCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

생성물 1

HCID 178518684HCID 178518684, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine dihydro-chloride (46 mg, 0.15 mmol) and 4-(8-oxo-3-phenyl-7,8-dihydro-1,7-naphthyridin-2-yl)benzaldehyde (40 mg, 0.12 mmol) in dry DMF (0.5 mL) was added triethylamine (55 μL, 0.40 mmol). After stirring for 10 minutes acetic acid (70 μL, 1.20 mmol) was added and the mixture was stirred at room temperature over night. Then sodium triacetoxy borohydride (52 mg, 0.24 mmol) was added in one portion. After two hours the reaction was complete and some methanol was added. This reaction mixture was concentrated to a smaller volume and adsorbed on silica gel and purified by column chromatography eluting with 0.5-13% methanol/ethyl acetate (sat'd NH3). The appropriate fractions were combined and the solvents removed in vacuo. The residue was triturated with diethyl ether to give pure title compound as a white solid. 1H NMR (500 MHz, DMSO-d6): δ 14.34 (1H, br s), 11.56 (1H, d, J=5.6 Hz), 8.68 (1H, br s), 8.15 (1H, s), 8.03 (1H, m), 7.96 (1H, m), 7.50 (1H, br s), 7.22-7-38 (10H, m), 6.62 (1H, d, J=6.8 Hz), 3.49 (2H, s), 2.84 (2H, brm), 2.69 (1H, m), 2.07 (2H, brt, J=11 Hz), 1.94 (2H, m), 1.78 (2H, m). m/e (m+1): 540.3, 270.8 [(m+2)/2].

후처리

  1. additionwas added
  2. concentrationThis reaction mixture was concentrated to a smaller volume
  3. custompurified by column chromatography
  4. washeluting with 0.5-13% methanol/ethyl acetate (sat'd NH3)
  5. customthe solvents removed in vacuo
  6. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-9037820265ef48519a7ccc3bddba73ac
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910561B2

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