Water → HCID 86691441, compound

HRID 540303Notes

Reaction equation

HRID 540303 reaction equation
[F:1][C:2]([F:7])([CH2:5][NH2:6])[CH2:3][NH2:4].C(N(CC)CC)C.[Cl:15][C:16]1[N:25]=[C:24](Cl)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:27])[CH:22]=2)[N:17]=1.O>ClCCl>[Cl:15][C:16]1[N:25]=[C:24]([NH:4][CH2:3][C:2]([F:7])([F:1])[CH2:5][NH2:6])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:27])[CH:22]=2)[N:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 142564832,4-Dichloro-6-methylquinazolineHCID 199026522,2-Difluoropropane-1,3-diamine

Product 1

HCID 86691441HCID 86691441, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,2-difluoropropane-1,3-diamine (1.1 g, 10 mmol) and triethylamine (1.4 mL, 10 mol) in dichloromethane (15 mL) was added a solution of 2,4-dichloro-6-methylquinazoline (500 mg, 2.36 mmol) in dichloromethane (5 mL) dropwise. After being stirred at room temperature overnight, the resulting mixture was poured into water (50 mL) and extracted with dichloromethane (50 mL×2). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 10-25% methanol in dichloromethane) to afford 41.8 mg of the desired product as a white solid (yield was 62%). MS obsd. (ESI+) [(M+H)+] 287.

Workup

  1. extractionextracted with dichloromethane (50 mL×2)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography (eluting with 10-25% methanol in dichloromethane)

Sources & evidence

ORD record
ord-8ee1d740f6b44f55b8527c704a8e4829
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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