1-Propanol, 3-amino-2,2-dimethyl- → HCID 69482007, compound

HRID 2364391Notes

Reaction equation

HRID 2364391 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33](OCC)=[O:34])[C:15]1=[O:38].[NH2:39][CH2:40][C:41]([CH3:45])([CH3:44])[CH2:42][OH:43]>CCO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[N:19][CH:20]=[C:21]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:22]=2)[C:17]([OH:32])=[C:16]([C:33]([NH:39][CH2:40][C:41]([CH3:45])([CH3:44])[CH2:42][OH:43])=[O:34])[C:15]1=[O:38]

Participants

4

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 69480967ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482007HCID 69482007, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (0.025 g, 0.049 mmol) in EtOH (1 mL) under nitrogen was treated with 3-amino-2,2-dimethyl-1-propanol (0.008 mL, 0.078 mmol) for 20 min. (160° C. in a microwave vessel. The reaction was further microwaved for 40 min.@160° C., cooled to ambient temperature, and the resulting suspension was filtered, washed with EtOH and then thoroughly dried under high vacuum to provide the title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 0.57 (s, 6 H), 1.93 (s, 1 H), 2.91 (d, J=5.19 Hz, 2 H), 3.08 (d, J=5.62 Hz, 2 H), 3.92 (t, J=5.33 Hz, 2 H), 4.16 (s, 2 H), 4.56-4.68 (m, 3 H), 7.11-7.18 (m, 2 H), 7.35-7.41 (m, 2 H), 7.80 (s, 4 H), 8.22 (d, J=0.84 Hz, 1 H), 8.55 (d, J=0.56 Hz, 1 H), 10.02 (t, J=6.32 Hz, 1 H); ES+ MS: 573 (M+H+).

Workup

  1. customThe reaction was further microwaved for 40 min.@160° C.
  2. filtrationthe resulting suspension was filtered
  3. washwashed with EtOH
  4. customthoroughly dried under high vacuum

Sources & evidence

ORD record
ord-b17af0a044ba4dfdb2e316c01b78376e
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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