2-Morpholinoethylamine → HCID 44143344, compound

HRID 2113571Notes

Reaction equation

HRID 2113571 reaction equation
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:10][C:11]1[CH:12]=[C:13]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][N:25]=[C:26](F)[CH:27]=3)[N:22]=[CH:21][C:20]=2[C:30]#[N:31])[CH:14]=[CH:15][C:16]=1[F:17]>N1C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([NH:18][C:19]2[C:28]3[C:23](=[CH:24][N:25]=[C:26]([NH:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:27]=3)[N:22]=[CH:21][C:20]=2[C:30]#[N:31])[CH:14]=[CH:15][C:16]=1[F:17]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 44143344HCID 44143344, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-morpholin-4-yl-ethylamine (0.44 mL, 2.73 mmol) and 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile (0.50 g, 1.58 mmol) in pyridine 5.3 mL was heated to 80° C. for 7 days. The solvent was evaporated and the crude product was purified by flash column chromatography (7% MeOH in CHCl3) to give a yellow solid (0.18 g, 44%). 1H NMR (400 MHz, CDCl3) δ 2.5 (m, 4 H) 2.6 (d, J=11.9 Hz, 2 H) 3.2 (m, 2 H) 3.7 (m, 4 H) 5.5 (t, J=5.1 Hz, 1 H) 6.2 (s, 1 H) 6.9 (s, 1 H) 7.1 (m, 1 H) 7.2 (t, J=8.6 Hz, 1 H) 7.3 (m, 1 H) 8.5 (s, 1 H) 9.1 (d, J=0.5 Hz, 1 H).

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by flash column chromatography (7% MeOH in CHCl3)

Sources & evidence

ORD record
ord-273edaae82f944a497d78c56431a5e71
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

Loading…