Methanesulfonyl chloride → HCID 69482601, compound

HRID 2364416Notes

Reaction equation

HRID 2364416 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][CH2:28][N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:24])[C:5]1=[O:35].C(N(C(C)C)CC)(C)C.[CH3:45][S:46](Cl)(=[O:48])=[O:47]>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][CH2:28][N:29]4[CH2:30][CH2:31][O:32][CH2:33][CH2:34]4)=[O:24])[C:5](=[O:35])[N:4]3[CH2:3][CH2:2][NH:1][S:46]([CH3:45])(=[O:48])=[O:47])=[N:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69482012HCID 69482012, compound

Product 1

HCID 69482601HCID 69482601, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-aminoethyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-[3-(4-morpholinyl)propyl]-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, and dried in vacuo to provide the title compound as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.67 (s, 1 H), 1.99 (br. s., 2 H), 2.90 (s, 3 H), 3.07 (d, J=12.07 Hz, 2 H), 3.12-3.28 (m, 4 H), 3.39-3.51 (m, 4 H), 3.59-3.72 (m, 2 H), 3.92-4.04 (m, 1 H), 4.15 (s, 2 H), 4.35 (t, J=7.23 Hz, 2 H), 7.09-7.17 (m, 2 H), 7.29 (t, J=6.60 Hz, 1 H), 7.35-7.44 (m, 2 H), 8.13 (s, 1 H), 8.56 (d, J=1.40 Hz, 1 H), 9.80 (br. s., 1 H), 10.31 (t, J=5.83 Hz, 1 H); ES+ MS: 562 (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. dry with materialMeOH, and dried in vacuo

Sources & evidence

ORD record
ord-4664afc6cdfd4971bea63774accd69c2
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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