N-Aminomorpholine → HCID 46929147, compound

HRID 1514722Notes

Reaction equation

HRID 1514722 reaction equation
O.OC1C2N=NNC=2C=CC=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](O)=[O:53])=[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].[NH2:59][N:60]1[CH2:65][CH2:64][O:63][CH2:62][CH2:61]1>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:59][N:60]4[CH2:65][CH2:64][O:63][CH2:62][CH2:61]4)=[O:53])=[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 20315N-AminomorpholineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66718168HCID 66718168, compoundHCID 178526939HCID 178526939, compound

Product 1

HCID 46929147HCID 46929147, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hydroxybenzotriazole hydrate (64.7 mg, 0.41 mmol), N-ethyldiisopropylamine (181 ul, 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 4-aminomorpholine (41.5 μL, 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 (130 mg, 70%) as a white solid. MS: m/e=445.2 [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-bccb7286393e47529eed4a8268e180e1
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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