Water → 4,6-dichloro-N-[(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amine

HRID 1747606Notes

Reaction equation

HRID 1747606 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C@H:4]1[NH2:12].[N:13]1[C:20]([Cl:21])=[N:19][C:17](Cl)=[N:16][C:14]=1[Cl:15].CCN(C(C)C)C(C)C.O>C1COCC1>[Cl:15][C:14]1[N:13]=[C:20]([Cl:21])[N:19]=[C:17]([NH:12][C@@H:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:11][C@@H:3]2[O:2][CH3:1])[N:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7954Cyanuric chlorideHCID 81531DiisopropylethylamineHCID 28109796(1R,2S)-2-Methoxy-2,3-dihydro-1H-inden-1-amine

Product 1

HCID 866187144,6-dichloro-N-[(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]-1,3,5-triazin-2-amineYield 49.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (1R,2S)-2-methoxyindan-1-amine (242.8 mg, 0.001488 mol) in THF (1 mL) was added cyanuric chloride (313 mg, 0.00170 mol) at 0° C., followed by DIPEA (300 μL, 0.002 mol) and the reaction was stirred at 0° C. for 1.5 hours. The reaction was poured into water and extracted with CH2Cl2. The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 15% EtOAc/hexanes) to obtain 229.1 mg (49%) of the title compound. LC/MS: Rt=2.03 min, ES+ 311 (FA standard).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0 to 15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8b17b5cc81b64d72861a9ca85ef00291
Source dataset
uspto-grants-2015_10
Patent number
US09150525B2

Reaction notes

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