Diisopropylethylamine → HCID 178431741, compound

HRID 1961378Notes

Reaction equation

HRID 1961378 reaction equation
C(N(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:27][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])=[CH:30][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][C:28]([F:27])=[CH:29][CH:30]=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 178431741HCID 178431741, compoundYield 67.1%

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 1C (860 mg, 64%) as a TFA salt. LC/MS [M+H]+: 458; Ret time (Method F): 2.70 min.

Workup

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

Sources & evidence

ORD record
ord-029f2c60e6ee45b6b1603c6235ec88ea
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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