Acetic Acid → HCID 66712130, compound

HRID 1262012Notes

Reaction equation

HRID 1262012 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH:12]=O)[N:5]2[N:4]=1.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C.C(Cl)Cl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]2=[CH:9][CH:10]=[C:11]([CH2:12][NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:5]2[N:4]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 6115AnilineHCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 574160572-(Methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine-7-carbaldehyde

Product 1

HCID 66712130HCID 66712130, compoundYield 99.6%

Procedure

2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine-7-carbaldehyde (0.200 g, 1.04 mmol) and Aniline (0.104 mL, 1.14 mmol) were dissolved in a solution of Acetic acid (0.100 mL, 1.76 mmol) and Methylene chloride (10 mL, 200 mmol) and the reaction was allowed to stir at room temperature for 1 hour. Sodium triacetoxyborohydride (0.439 g, 2.07 mmol) was then added and the reaction was allowed to continue stirring at room temperature until HPLC showed consumption of starting material. The reaction mixture was poured over saturated sodium bicarbonate and organics were extracted with dichloromethane. Combined extracts were then dried over sodium sulfate, filtered and reduced. The crude reaction mixture was then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent) and combined fractions were reduced and dried under vacuum to afford 0.280 g of (2-Methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-ylmethyl)-phenyl-amine. 1H NMR (400 MHz, DMSO, d6) δ 8.92 (s, 1H), 7.06 (m, 2H), 6.90 (d, 1H, J=4.61 Hz), 6.83 (d, 1H, J=4.61 Hz), 6.65 (m, 2H), 6.54 (t, 1H, J=7.28 Hz), 6.13 (t, 1H, J=6.16 Hz), 4.61 (d, 2H, J=6.16 hz), 2.56 (s, 3H).

Workup

  1. stirringto continue stirring at room temperature until HPLC
  2. customconsumption of starting material
  3. additionThe reaction mixture was poured over saturated sodium bicarbonate
  4. extractionorganics were extracted with dichloromethane
  5. dry with materialCombined extracts were then dried over sodium sulfate
  6. filtrationfiltered
  7. customThe crude reaction mixture
  8. customwas then purified by Isco flash column chromatography (hexanes/ethyl acetate eluent)
  9. customdried under vacuum

Sources & evidence

ORD record
ord-52fecdc949c840b9b51dcb3132a4bd49
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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