Trifluoroacetic acid → 3-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amine

HRID 2390688Notes

Reaction equation

HRID 2390688 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17]C(=O)OC(C)(C)C)=[C:13]([O:25][CH3:26])[CH:12]=3)=[CH:9][O:10][C:6]=2[C:5]([I:27])=[CH:4][N:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[C:7]3[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([I:27])[C:6]=3[O:10][CH:9]=2)=[CH:12][C:13]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18451460Tert-butyl 4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate

Product 1

HCID 184507093-(4-Amino-3-methoxyphenyl)-7-iodofuro[3,2-c]pyridin-4-amineYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 4-(4-amino-7-iodofuro[3,2-c]pyridin-3-yl)-2-methoxyphenylcarbamate (3.98 g, 8.28 mmol) was added to a 20% solution of trifluoroacetic acid in dichloro-methane (150 mL). The mixture was stirred for two hours and then the solvent was removed in vacuo. To the residue was added water (15 mL) and dichloromethane (25 mL). The mixture was adjusted to pH 12 with 1 N aqueous sodium hydroxide and the layers were separated. The aqueous layer was extracted with dichloromethane (2×10 mL) and the combined organic layers were dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to give the title compound (2.534 g 80%). 1H NMR (DMSO-d6, 400 MHz) □ 8.03 (s, 1H) 7.94 (s, 1H) 6.91 (d, 1H), 6.82 (dd, 1H), 6.75 (d, 1H), 5.69-5.77 (bs, 2H), 4.96-5.05 (bs, 2H), 3.81 (s, 3H); RP-HPLC (Conditions f) Rt 11.22 min.; MS: MH+ 382.

Workup

  1. customthe solvent was removed in vacuo
  2. additionTo the residue was added water (15 mL) and dichloromethane (25 mL)
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane (2×10 mL)
  5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-de553c7e5fa74528a112af4ff3bc32ff
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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