Methanesulfonyl chloride → HCID 69482205, compound

HRID 2364420Notes

Reaction equation

HRID 2364420 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=2)[C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])=[O:24])[C:5]1=[O:32].C(N(C(C)C)CC)(C)C.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>CN(C=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][C:11]2[CH:12]=[C:13]3[C:8]([C:7]([OH:22])=[C:6]([C:23]([NH:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][OH:31])=[O:24])[C:5](=[O:32])[N:4]3[CH2:3][CH2:2][NH:1][S:43]([CH3:42])(=[O:45])=[O:44])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69482715HCID 69482715, compound

Product 1

HCID 69482205HCID 69482205, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-{2-[(2-hydroxyethyl)oxy]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (0.025 g, 0.052 mmol) and diisopropyl ethylamine (0.05 mL, 0.29 mmol) in DMF (5 mL) under nitrogen was treated with methanesulfonyl chloride (0.0053 mL, 0.068 mmol) at 40° C. for 1 h then 3½ h at ambient temperature. The reaction was concentrated in vacuo and the resulting residue was triturated with Et2O:MeOH, filtered, washed with 2:1 Et2O:MeOH. A second crop was obtained by filtration from the filtrate, dried in vacuo to provide the title compound as an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.90 (s, 3 H), 3.19-3.30 (m, 2 H), 3.46-3.61 (m, 8 H), 4.14 (s, 2 H), 4.34 (t, J=6.53 Hz, 2 H), 4.60-4.64 (m, 1 H), 7.09-7.16 (m, 2 H), 7.23-7.29 (m, 1 H), 7.37-7.44 (m, 2 H), 8.11 (d, J=0.84 Hz, 1 H), 8.55 (d, J=1.54 Hz, 1 H), 10.35 (t, J=5.48 Hz, 1 H), 17.12 (s, 1 H); ES+ MS: 523 (M+H+).

Workup

  1. custom3½ h
  2. customat ambient temperature
  3. concentrationThe reaction was concentrated in vacuo
  4. customthe resulting residue was triturated with Et2O
  5. filtrationMeOH, filtered
  6. washwashed with 2:1 Et2O
  7. customA second crop was obtained by filtration from the filtrate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-024d1c14af604315ac656fb8bb780456
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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