2-Morpholinoethylamine → HCID 69184561, compound

HRID 2113598Notes

Reaction equation

HRID 2113598 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:9](F)=[N:8][CH:7]=2)#[N:2].[NH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>O1CCCC1>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=[CH:10][C:9]([NH:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)=[N:8][CH:7]=2)#[N:2]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 69180804HCID 69180804, compound

Product 1

HCID 69184561HCID 69184561, compoundYield 159.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described above in Example 1, methyl 3-(3-cyano-6-fluoro-1,7-naphthyridin-4-ylamino)benzoate (0.25 g, 0.78 mmol, 1 eq) was reacted with 4-(2-aminoethyl)morpholine (1 mL, 7.62 mmol, 9.8 eq) in tetrahydrofuran (4 mL). Workup and flash column chromatography eluting with 2-5% methyl alcohol in dichloromethane yielded 539 mg product (54% yield): 1H NMR (400 MHz, DMSO-D6) δ ppm 2.40-2.46 (m, 4 H) 2.55 (t, J=6.44 Hz, 2 H) 3.34-3.39 (m, 2 H) 3.54-3.60 (m, 4 H) 3.87 (s, 3 H) 6.67 (t, J=5.18 Hz, 1 H) 7.01 (s, 1 H) 7.56 (dt, J=4.36, 1.23 Hz, 2 H) 7.79-7.83 (m, 2 H) 8.32 (s, 1 H) 8.87 (s, 1 H) 9.73 (s, 1 H).

Workup

  1. washWorkup and flash column chromatography eluting with 2-5% methyl alcohol in dichloromethane

Sources & evidence

ORD record
ord-7b06fa0865bd42a2a96e15208c4a527a
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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