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Acetic Acid → HCID 178478337, 화합물

HRID 1678762
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HRID 1678762 반응식
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)=[N:7]2.Cl.Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([C:34]2[N:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[NH:36][N:35]=2)[CH2:30][CH2:29]1.C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1C(=O)CCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:6]([C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:28]3[CH2:33][CH2:32][CH:31]([C:34]4[NH:38][C:37]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=5)=[N:36][N:35]=4)[CH2:30][CH2:29]3)=[CH:14][CH:13]=1)=[N:7]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 575007324-(5-Chloro-3-phenyl-1,6-naphthyridin-2-yl)benzaldehydeHCID 1784785342-(5-Piperidin-4-yl-4h-1,2,4-triazol-3-yl)-pyridine dihydrochloride

생성물 1

HCID 178478337HCID 178478337, 화합물

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a stirred solution of 9-1 (4.9 g, 14.2 mMol) and 8-5 (4.2 g, 15.6 mMol) in NMP (50 mL) was added triethylamine (6 mL, 42.6 mMol) followed by acetic acid (1.6 mL, 28.4 mMol). After stirring at ambient temperature overnight, sodium triacetoxyborohydride (3.6 g, 17 mMol) was added in portions. Upon completion, the reaction was diluted with ethyl acetate and washed with saturated NaHCO3, followed by water, then brine. The organic layer was dried with Na2SO4 and MgSO4, filtered and concentrated in vacuo. The crude residue purified using flash chromatography on silica (gradient: 0% to 10% MeOH in CHCl3 over 25 min) to yield 9-2 as an orange solid. LC/MS (M+1) calculated: 559.1; observed: 559.2

후처리

  1. washwashed with saturated NaHCO3
  2. dry with materialThe organic layer was dried with Na2SO4 and MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue purified
  6. customon silica (gradient: 0% to 10% MeOH in CHCl3 over 25 min)

출처 및 근거

ORD 기록
ord-46d5555773404055a69342c57682b8c5
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08008317B2

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