1-Pyrrolidinamine → HCID 46929148, compound

HRID 1514723Notes

Reaction equation

HRID 1514723 reaction equation
O.O[C:3]1[C:11]2[N:10]=[N:9]NC=2C=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.Cl.CN(C)CCCN=C=NCC.[F:33][C:34]1[CH:35]=[C:36]([C:41]2[C:45]([CH2:46][O:47][C:48]3[CH:56]=[CH:55][C:51]([C:52]([OH:54])=O)=[CH:50][N:49]=3)=[C:44]([CH2:57][OH:58])[O:43][N:42]=2)[CH:37]=[CH:38][C:39]=1[F:40].NN1CCCC1>C1COCC1>[F:33][C:34]1[CH:35]=[C:36]([C:41]2[C:45]([CH2:46][O:47][C:48]3[CH:56]=[CH:55][C:51]([C:52]([NH:9][N:10]4[CH2:5][CH2:4][CH2:3][CH2:11]4)=[O:54])=[CH:50][N:49]=3)=[C:44]([CH2:57][OH:58])[O:43][N:42]=2)[CH:37]=[CH:38][C:39]=1[F:40]

Participants

7

Reactant 5

HCID 279461-PyrrolidinamineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66718168HCID 66718168, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 46929148HCID 46929148, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxybenzotriazole hydrate (64.7 mg; 0.41 mmol), N-ethyldiisopropylamine (181 μL, 1.04 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (81 mg, 0.41 mmol) were added to a mixture of 6-[3-(3,4-difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid (150 mg, 0.41 mmol) and 1-aminopyrrolidine (51.8 mg, 0.41 mmol) in THF (15 mL) at room temperature. After stirring overnight the solvent was removed by distillation and the residue was purified by chromatography (silica, dichloromethane:methanol=98:2 to 95:5) afforded the title compound (150 mg, 84%) as a white solid. MS: m/e=429.1 [M−H]−.

Workup

  1. customwas removed by distillation
  2. customthe residue was purified by chromatography (silica, dichloromethane:methanol=98:2 to 95:5)

Sources & evidence

ORD record
ord-76108109880b472f9cc3445ac23c3f3c
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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