Ammonia → HCID 178511910, compound

HRID 1668467Notes

Reaction equation

HRID 1668467 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([NH2:16])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:2]=1.I.[S:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23](SC)=[NH:24].N>CCO.CO.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[C:15]3[C:10](=[CH:11][C:12]([NH:16][C:23]([C:19]4[S:18][CH:22]=[CH:21][CH:20]=4)=[NH:24])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)[CH:2]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 18005103HCID 18005103, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511910HCID 178511910, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of compound 73 (275 mg, 1.32 mmol) in 15 mL EtOH was treated with methyl thiophene-2-carbimidothioate hydroiodide (750 mg, 2.63 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was diluted with CH2Cl2 (50 mL) and treated with saturated sodium bicarbonate (20 mL). The organic layer was separated and the aqueous layer was extracted with an additional 50 mL CH2Cl2. The combined organic layers were dried over sodium sulfate and concentrated to give a yellow solid which was subjected to flash chromatography on silica gel using 5% MeOH/CH2Cl2 to 5% 2M NH3 in MeOH/CH2Cl2 to give an off-white residue, compound 74 (210 mg, 50%). HPLC analysis indicated that the product is >98% pure. 1H NMR (DMSO-d6) δ 8.85 (d, J=2.5 Hz, 1H), 8.58 (d, J=4.0 Hz, 1H), 8.08-8.05 (m, 1H), 7.75-7.53 (m, 5H), 7.12-7.09 (m, 2H), 6.78 (dd, J=1.5, 7.0 Hz, 1H), 6.67 (d, J=3.1 Hz, 1H), 6.35 (brs, 2H); ESI-MS (m/z, %): 319 (M+1, 100%); ESI-HRMS calculated for C18H15N4S (MH+): 319.1011, observed: 319.1015.

Workup

  1. customArgon was bubbled through the mixture for 20 minutes
  2. additionit was diluted with CH2Cl2 (50 mL)
  3. additiontreated with saturated sodium bicarbonate (20 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with an additional 50 mL CH2Cl2
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give a yellow solid which

Sources & evidence

ORD record
ord-c5cf1a87cc264145bb6a2f3d1b3468e2
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

Loading…