Methanol → 2-Chloro-5-phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile

HRID 2219075ノート

反応式

HRID 2219075 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][C:12]([C:13]#[N:14])=[C:11]([Cl:23])[N:10]=2)=[CH:5][CH:4]=1.CO.[S:26]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([CH2:37][NH2:38])=[CH:33][CH:32]=2)[N:28]=[N:27]1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:23][C:11]1[N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][NH:38][CH2:37][C:34]3[CH:33]=[CH:32][C:31]([C:29]4[N:28]=[N:27][S:26][CH:30]=4)=[CH:36][CH:35]=3)=[CH:4][CH:5]=2)[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:15][C:12]=1[C:13]#[N:14]

参加物

6

反応物 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 27372881-[4-(1,2,3-Thiadiazol-4-Yl)phenyl]methanamineHCID 866076536-[4-(Bromomethyl)phenyl]-2-chloro-5-phenylnicotinonitrile

生成物 1

HCID 111911212-Chloro-5-phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 6-[4-(bromomethyl)phenyl]-2-chloro-5-phenylnicotinonitrile (2-5) 0.294 g, 0.766 mmol) in THF (5 mL) and MeOH (5 mL) was added 1-[4-(1,2,3-thiadiazol-4-yl)phenyl]methanamine (0.147 g, 0.766 mmol) and DIPEA (0.495 g, 3.831 mmol). The mixture wsa stirred overnight and concentrated. The residue was treated with aqueous Na2CO3 solution (2 M, 10 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic layer was dried, filtered and concentrated. The residue was purified by silica gel chromatography (3-6% MeOH in CH2Cl2) to give 2-chloro-5-phenyl-6-[4-({[4-(1,2,3-thiadiazol-4-yl)benzyl]amino}methyl)phenyl]nicotinonitrile (2-6). 1H-NMR (500 MHz, CDCl3) δ 8.63 (s, 1H), 8.01 (d, J=8.0, 2H), 7.98 (s, 1H), 7.47 (d, J=8.1, 2H), 7.28-7.38 (m, 7H), 7.16-7.18 (m, 2H), 3.84 (s, 2H), 3.83 (s, 2H). LRMS m/z (M+H) Calcd: 494.0, found: 494.1.

後処理

  1. concentrationconcentrated
  2. additionThe residue was treated with aqueous Na2CO3 solution (2 M, 10 mL)
  3. extractionextracted with CH2Cl2 (3×30 mL)
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (3-6% MeOH in CH2Cl2)

出典と根拠

ORDレコード
ord-1258dab66d2d4ca1a736bd5107230272
出典データセット
uspto-grants-2008_08
特許番号
US07414055B2

反応ノート

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