Methyl iodide → HCID 10095410, compound

HRID 1271879Notes

Reaction equation

HRID 1271879 reaction equation
IC.[CH2:3]([N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=[C:11]1[CH:22]([N:26]1[C:32](=[O:33])[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[CH:23]([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:34]CN(CC)CC>C(Cl)Cl>[CH2:3]([N:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([Cl:21])=[CH:16][CH:17]=2)[N:12]=[C:11]1[CH:22]([N:26]1[C:32](=[O:33])[CH2:31][CH2:30][N:29]([CH3:34])[CH2:28][CH2:27]1)[CH:23]([CH3:25])[CH3:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 9932869HCID 9932869, compound

Product 1

HCID 10095410HCID 10095410, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Iodomethane (23 μL, 0.37 mmol) was added to a solution containing 3-benzyl-7-chloro-2-[2-methyl-1-(7-oxo-[1,4]diazepan-1-yl)-propyl]-3H-quinazolin-4-one and Et3N (51.4 μL, 0.37 mmol) in CH2Cl2 (5 mL). The resulting mixture was stirred at RT overnight, diluted with CH2Cl2 (5 mL), washed with brine, dried and concentrated under vacuum. Purification by flash chromatography on silica gel (1–2% CH3OH in CH2Cl2) gave the title compound (65 mg, 70%) as a pale yellow solid: MS (ES) m/e 453.0 (M+H)+.

Workup

  1. washwashed with brine
  2. customdried
  3. concentrationconcentrated under vacuum
  4. customPurification by flash chromatography on silica gel (1–2% CH3OH in CH2Cl2)

Sources & evidence

ORD record
ord-2c031d6bf3904c76bb51bccb83d3ad06
Source dataset
uspto-grants-2007_04
Patent number
US07208487B2

Reaction notes

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