N-methyl-2-pyrrolidone → HCID 86619124, compound

HRID 2109982Notes

Reaction equation

HRID 2109982 reaction equation
[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])C.CN(C(ON1N=NC2[CH:21]=[CH:22][CH:23]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)[CH:36]1[CH2:40]CN[CH2:37]1.[CH3:42][N:43]1[C:47](=[O:48])[CH2:46][CH2:45][CH2:44]1>>[C:7]1([N:3]2[CH2:2][CH2:1][CH2:21][CH2:22][CH2:23][CH2:44][CH2:45][CH2:46][C:47](=[O:48])[NH:43][CH2:42][CH2:6][CH2:4]2)[CH:8]=[CH:40][CH:36]=[CH:37][CH:9]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 27585193-(Dimethylamino)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×

Product 1

HCID 86619124HCID 86619124, compound

Procedure

To a mixture of compound (17 a) (35 mg, 0.075 mmol), DIEA (50 μL) in 1 mL of NMP was added HATU (50 mg, 0.12 mmol). The reaction mixture was sonicated for 2 min, and allowed to stand for 0.5 h at room temperature After which, dimethyl-pyrrolidin-3-yl-amine (15 μL. 0.1 mmol) was added, followed by additional HATU (5 mg. 0.12 mmol). The reaction mixture was stirred at room temperature for 0.5 h. Preparative RP-HPLC purification provided (11,14)3,5N-{[(3-dimethylamino-pyrrolidine-1-carbonyl)-phen-3-yl]pyrazolo[1,5-a]pyrimidin-2,4-yl-diamino}-(2N,4N)-phenyl-1,5-diaza-cyclotetradecan-6-one (18a) (15 mg).

Workup

  1. customThe reaction mixture was sonicated for 2 min
  2. customPreparative RP-HPLC purification

Sources & evidence

ORD record
ord-099f389f8fa64345a625a720ca4aa6e7
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

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