Diisopropylethylamine → (S)-1-(4-Chloro-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)-1,3,5-triazin-2-yl)-2-methyl-N-(pyrazin-2-yl)pyrrolidine-2-carboxamide

HRID 1961380Notes

Reaction equation

HRID 1961380 reaction equation
C([N:4](C(C)C)CC)(C)C.Cl[C:11]1[N:16]=[C:15]([Cl:17])[N:14]=[C:13]([NH:18][C:19]2[NH:23][N:22]=[C:21]([CH:24]3[CH2:26][CH2:25]3)[CH:20]=2)[N:12]=1.F[C:28]1[N:33]=[CH:32][C:31]([NH:34][C:35]([C@:37]2([CH3:42])[CH2:41][CH2:40][CH2:39][NH:38]2)=[O:36])=C[CH:29]=1>C1COCC1>[Cl:17][C:15]1[N:14]=[C:13]([NH:18][C:19]2[NH:23][N:22]=[C:21]([CH:24]3[CH2:26][CH2:25]3)[CH:20]=2)[N:12]=[C:11]([N:38]2[CH2:39][CH2:40][CH2:41][C@@:37]2([CH3:42])[C:35]([NH:34][C:31]2[CH:32]=[N:33][CH:28]=[CH:29][N:4]=2)=[O:36])[N:16]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59436446(S)-N-(6-Fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamideHCID 178478357HCID 178478357, compound

Product 1

HCID 178431749(S)-1-(4-Chloro-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)-1,3,5-triazin-2-yl)-2-methyl-N-(pyrazin-2-yl)pyrrolidine-2-carboxamideYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (0.77 mL, 4.42 mmol) was added to a mixture of 4,6-dichloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)-1,3,5-triazin-2-amine (800 mg, 2.95 mmol) and (S)—N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide (625 mg, 2.8 mmol) in THF (20 mL). The reaction mixture was stirred at room temperature overnight and the product was separated by preparative HPLC. Removal of the solvents furnished 8B (860 mg, 64%) as a TFA salt. LC/MS [M+H]+: 440; Ret time (Method C): 2.33 min.

Workup

  1. customthe product was separated by preparative HPLC
  2. customRemoval of the solvents

Sources & evidence

ORD record
ord-f51173a9fffc482eb94460975561134f
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

Loading…