2,4-Dichloro-1,3,5-triazine → HCID 89155990, compound

HRID 1405207Notes

Reaction equation

HRID 1405207 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[CH:18]1([S:23]([CH2:26][C:27]2[CH:28]=[C:29]([CH:31]=[CH:32][CH:33]=2)[NH2:30])(=[O:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1>C1COCC1.CC(O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:30][C:29]2[CH:31]=[CH:32][CH:33]=[C:27]([CH2:26][S:23]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)(=[O:25])=[O:24])[CH:28]=2)[N:7]=1

Participants

5

Reactant 3

HCID 178102,4-Dichloro-1,3,5-triazineHCID 81531DiisopropylethylamineHCID 63114873HCID 63114873, compound

Product 1

HCID 89155990HCID 89155990, compoundYield 205.7%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

To a stirred solution of 2,4-dichloro-1,3,5-triazine (150 mg, ABCR GmbH & CO. KG) in THF/i-PrOH (1:1; 1.9 mL) DIPEA (0.35 mL) was added at −40° C. Then a suspension of 3-[(cyclopentylsulfonyl)methyl]aniline (240 mg) in THF/2-PrOH (1:1, 0.94 mL) was added at this temperature. Under stirring the temperature of the reaction mixture was slowly raised over 2 hours to 0° C. The reaction mixture was then concentrated in vacuo to give the crude title compound (726 mg) which was used without further purification.

Workup

  1. additionwas added at this temperature
  2. temperaturewas slowly raised over 2 hours to 0° C
  3. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-a3329cf9b70d4b138c34d1241e7e47c4
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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