Sodium Thiosulfate → Tert-butyl 4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate

HRID 17191

反応式

HRID 17191 の反応式
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:15]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:21]([O:33][CH3:34])[CH:20]=3)=[CH:17][O:18][C:14]=2[CH:13]=[CH:12][N:11]=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[NH2:9][C:10]1[C:15]2[C:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[C:21]([O:33][CH3:34])[CH:20]=3)=[CH:17][O:18][C:14]=2[C:13]([I:1])=[CH:12][N:11]=1

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 18451465Tert-butyl 4-(4-aminofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate

生成物 1

HCID 18451460Tert-butyl 4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate収率 84%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

N-Iodosuccinimide (0.333 g, 1.48 mmol) was added to a solution of tert-butyl 4-(4-aminofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate (0.439 g, 1.24 mmol) in N,N-dimethylformamide (10 mL) at ambient temperature. The reaction suspension was stirred for 18 hours, at which time no starting material remained. An aqueous solution of 10% sodium thiosulfate (10 mL) was added to the suspension and stirred for 30 minutes. The precipitate was collected by vacuum filtration and washed with water. The solid was dried in vacuo to give the title compound (0.501 g, 84%) as a tan solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.08 (s, 1H), 8.07 (s, 1H), 8.06 (s, 1H), 7.85 (d, 1H), 7.13 (d, 1H), 7.04, (dd, 1H), 5.73-5.80 (bs, 2H), 3.86 (s, 3H), 1.48 (s, 9H); RP-HPLC (Conditions d) Rt 8.49 min.; MS: MH+ 482.

後処理

  1. stirringstirred for 30 minutes
  2. filtrationThe precipitate was collected by vacuum filtration
  3. washwashed with water
  4. customThe solid was dried in vacuo

出典と根拠

ORDレコード
ord-c8c124ac2a8e4858b3b50ed0ef9d7251
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

関連ノート

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