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Acetic Acid → HCID 178478337、化合物

HRID 1678762
ノート
印刷プレビュー

反応式

HRID 1678762 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 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

生成物 1

HCID 178478337HCID 178478337、化合物

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-46d5555773404055a69342c57682b8c5
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08008317B2

反応ノート

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