Dichloromethane → HCID 21897027, compound

HRID 719423Notes

Reaction equation

HRID 719423 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[N:21]=[C:20]([NH:22][CH:23]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[N:19]=[C:18]([N:30]([CH3:37])[CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[N:17]=2)=[CH:11][C:10]=1Cl)C1C=CC=CC=1.C([O-])=O.[NH4+].C(Cl)Cl>O.CO.[Pd]>[CH:23]1([NH:22][C:20]2[N:19]=[C:18]([N:30]([CH3:37])[CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[N:17]=[C:16]([NH:15][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[N:21]=2)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 2723923Ammonium formateHCID 21896940HCID 21896940, compound

Product 1

HCID 21897027HCID 21897027, compoundYield 47.6%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×

Procedure

In a dry round bottomed flask was added 10% Pd/C (301.5 mg) and was wetted with 3–5 drops of water. Nitrogen was blown over the Pd/C for about 5 minutes, then methanol (10 mL) was added cautiously and nitrogen was blown on the mixture for another 5 minutes. Triazine E3 (251.8 mg, 0.50 mmol) dissolved in methanol (5 mL) was added followed by ammonium formate (381.5 mg, 6.0 mmol), and the reaction was stirred and heated reflux for about 1.5 hours. Methylene chloride was added and allowed to cool to room temperature. The mixture was filtered by vacuum through Celite with a methylene chloride rinsing and the filtrate was concentrated in vacuo. The material was purified by silica gel flash chromatography eluting with 90:9:1 by volume methylene chloride:methanol:ammonium hydroxide, and the collected fractions were dried over anhydrous magnesium sulfate, filtered and then concentrated in vacuo to give a light yellow solid (E4) (98 mg, 44%); mp 130° C.; HPLC: Inertsil ODS 3V C18, 40:30:30 [KH2PO4(0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 3.2 min, 99.6% purity; MS (TOF ES+) m/z 412 (M+H, 100), 235.6 (87.2), 206.6 (16.1).

Workup

  1. additionwas added
  2. temperatureheated
  3. temperaturereflux for about 1.5 hours
  4. filtrationThe mixture was filtered by vacuum through Celite with a methylene chloride rinsing
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe material was purified by silica gel flash chromatography
  7. washeluting with 90:9:1 by volume methylene chloride
  8. dry with materialmethanol:ammonium hydroxide, and the collected fractions were dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1483161c950c483d858e17498516e075
Source dataset
uspto-grants-2006_11
Patent number
US07132423B2

Reaction notes

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