HCID 59004626, compound → HCID 178511911, compound

HRID 1668470Notes

Reaction equation

HRID 1668470 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.I.[S:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](SC)=[NH:25]>CCO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:24]([C:20]4[S:19][CH:23]=[CH:22][CH:21]=4)=[NH:25])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 59004626HCID 59004626, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178511911HCID 178511911, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 76 (120 mg, 0.53 mmol) in EtOH (5 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (183 mg, 0.64 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then the suspension 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 CH2Cl2 (50 mL). 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 (MeOH:CH2Cl2, 5:95 to 2M NH3 in MeOH:CH2Cl2, 5:95) to give compound 77 (86 mg, 48.9%) as a yellow solid. HPLC analysis indicated that the product is >99% pure. 1H NMR (DMSO-d6) δ 8.06 (d, J=2.5 Hz, 1H), 7.72 (d, J=3.4 Hz, 1H), 7.60-7.50 (m, 2H), 7.42 (d, J=3.0 Hz, 1H), 7.11-7.06 (m, 2H), 6.71 (d, J=8.9 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H), 6.53 (d, J=3.0, 1H), 6.30 (brs, 2H), 6.16 (brs, 2H); ESI-MS (m/z, %): 334 (M+1, 100%); ESI-HRMS calculated for C18H16N5S (MH+): 334.1120, observed: 334.1135.

Workup

  1. customArgon was bubbled through the mixture for 20 minutes
  2. additionthe suspension 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 CH2Cl2 (50 mL)
  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-b14283837e264dbbae51049568df8663
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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