Dimethylformamide → HCID 58034611, compound

HRID 1914856Notes

Reaction equation

HRID 1914856 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]2[N:16]=[CH:15][C:14]3[CH:13]=[C:12]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[C:11](=O)[NH:10][C:9]=3[N:8]2[N:24]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:27])=O.CN(C=O)C>C(Cl)(Cl)Cl>[Cl:27][C:11]1[N:10]=[C:9]2[C:14]([CH:15]=[N:16][C:7]3[N:8]2[N:24]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=3)=[CH:13][C:12]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6228Dimethylformamide2×HCID 24386Thionyl Chloride2×HCID 136133169HCID 136133169, compound

Product 1

HCID 58034611HCID 58034611, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a 100 mL three necked round bottom flask was added 2-tert-butyl-7-phenyl-9H-1,4,9,9b-tetraaza-cyclopenta[a]naphthalen-8-one (1 g, 3.14 mmol, 1.00 equiv), CHCl3 (20 mL), thionyl chloride (0.94 mL, 4.00 equiv) and DMF (48 μL, 0.20 equiv) and the resulting solution was stirred for 1 h at 70° C. under nitrogen. After 1 h, additional thionyl chloride (0.47 mL, 2.00 equiv) and DMF (48 μL, 0.20 equiv) was added and the resulting solution was stirred for an additional 2 h at 70° C. After a total of 3 h, the resulting mixture was concentrated under vacuum and the pH value of the solution was adjusted to 7 with saturated aqueous NaHCO3 solution. The resulting solution was extracted with ethyl acetate and the organic layers were combined and dried and concentrated under vacuum. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether as the eluent to give the Compound [CCXXXIX] as a yellow solid. 1H NMR (300 MHz, DMSO, δ, ppm) 9.09 (s, 1H), 8.74 (s, 1H), 7.60-7.52 (m, 5H), 6.97 (s, 1H), 1.44 (s, 91-1); LC-MS: m/z=337 (M+H)+.

Workup

  1. waitAfter 1 h
  2. stirringthe resulting solution was stirred for an additional 2 h at 70° C
  3. concentrationAfter a total of 3 h, the resulting mixture was concentrated under vacuum
  4. extractionThe resulting solution was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customto give the Compound [CCXXXIX] as a yellow solid

Sources & evidence

ORD record
ord-6b785bb9666a457083b4219de59a4f4f
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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