3-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine → N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-benzimidazole-2-carboxamide

HRID 1270919

반응식

HRID 1270919 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[C:13]([NH2:18])=[N:14][CH:15]=[C:16]([I:17])[C:11]=3[O:10][CH:9]=2)=[CH:4][C:3]=1[O:19][CH3:20].[CH3:21][N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[C:31](Cl)=[O:32]>N1C=CC=CC=1>[NH2:18][C:13]1[C:12]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:31]([C:23]4[N:22]([CH3:21])[C:26]5[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=5[N:24]=4)=[O:32])=[C:3]([O:19][CH3:20])[CH:4]=3)=[CH:9][O:10][C:11]=2[C:16]([I:17])=[CH:15][N:14]=1

참가 물질

4

반응물 2

HCID 184507093-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amineHCID 205432271-Methyl-1H-benzimidazole-2-carbonyl chloride

생성물 1

HCID 18451295N-[4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-benzimidazole-2-carboxamide수율 105.8%

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
0 °C

실험 절차

A solution of 3-(4-amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine (1.50 g, 3.94 mmol) in pyridine (18 mL) was cooled to 0° C. and 1-methyl-1H-benzo[d]imidazole-2-carbonyl chloride (0.874 g, 3.33 mmol) was added. The mixture was stirred for 15 minutes at 0° C. and then allowed to rise to ambient temperature over an eighteen hour time period. The solvent was removed in vacuo and the residue was suspended in water (50 mL) and brought to pH 12 with 0.1 N aqueous sodium hydroxide. The suspension was extracted with dichloromethane (4×25 mL) and the combined organic layers were washed with brine (25 mL) and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title compound (1.90 g, 90%) as a yellow solid. 1H NMR (DMSO-d6, 400 MHz.)δ 10.18 (s, 1H), 8.49 (d, 1H), 8.14 (s, 1H), 8.08 (s, 1H), 7.85 (d, 1H), 7.76 (d, 1H), 7.46 (t, 1H), 7.39 (t, 1H), 7.30 (s, 1H), 7.19 (d, 1H), 5.77–5.89 (b, 2H), 4.24 (s, 3H), 4.03 (s, 3H); RP-HPLC (Conditions d) Rt 11.89 min.; MS: MH+ 540.

후처리

  1. waitto rise to ambient temperature over an eighteen hour
  2. customThe solvent was removed in vacuo
  3. extractionThe suspension was extracted with dichloromethane (4×25 mL)
  4. washthe combined organic layers were washed with brine (25 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-a03d437eddd4489399c09bc23c4ab2e4
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202363B2

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