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

HRID 17191

Reaction equation

HRID 17191 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-c8c124ac2a8e4858b3b50ed0ef9d7251
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Linked notes

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