2-Thiophenecarbonyl chloride → HCID 11202878, compound

HRID 901231Notes

Reaction equation

HRID 901231 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](Cl)=[O:7].[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:37])[N:16]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:17]2[C:22]([C:23]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:13])[CH3:10]>N1C=CC=CC=1>[CH2:9]([O:11][C:12]([C:14]1[C:15](=[O:37])[N:16]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:17]2[C:22]([C:23]=1[N:24]1[CH2:25][CH2:26][N:27]([C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[O:7])[CH2:28][CH2:29]1)=[CH:21][CH:20]=[CH:19][N:18]=2)=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 59699580HCID 59699580, compound

Product 1

HCID 11202878HCID 11202878, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Thiophene carbonyl chloride (0.16 mL, 1.5 mmol) was added to a stirred solution of 1-benzyl-2-oxo-4-piperazin-1-yl-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (5) (392 mg, 1 mmol) in pyridine (5 mL) at 0° C. under inert atmosphere. The solution was allowed to come at room temperature and further stirred for 18 h. The solution was poured into ice water, the solids formed were filtered, washed by water, dried, and recrystallized by ether and ethyl acetate to yield 256 mg (51%) of 1-benzyl-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-2-oxo-1,2-dihydro-[1,8]-naphthyridine-3-carboxylic acid ethyl ester (6) as white solids. MP: 168° C.; 1H-NMR (DMSO-d6): δ 1.29 (t, J=6.9 Hz, 3H), 3.16 (m, 4H), 3.88 (m, 4H), 4.31 (q, J=6.9 Hz, 2H), 5.56 (s, 2H), 7.15 (dd, J=3.5, 4.9 Hz, 1H), 7.20-7.29 (m, 5H), 7.38 (dd, J=4.6, 8.2 Hz, 1H), 7.97 (d, J=4.9 Hz, 1H), 8.35 (dd, J=1.5, 7.5 Hz, 1H), 8.66 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 503 (M+1), 525 (M+23). Anal. C27H26N4O4S (C,H,N).

Workup

  1. customto come at room temperature
  2. customthe solids formed
  3. filtrationwere filtered
  4. washwashed by water
  5. customdried
  6. customrecrystallized by ether and ethyl acetate

Sources & evidence

ORD record
ord-2518439a763f4300b0a0832fd78de511
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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