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

HRID 2219075노트

반응식

HRID 2219075 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1258dab66d2d4ca1a736bd5107230272
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414055B2

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