5-Isocyanatoisoquinoline → HCID 10386145, compound

HRID 585998Notes

Reaction equation

HRID 585998 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:16])[C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][NH2:6].[N:17]([C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][N:24]=[CH:25]2)=[C:18]=[O:19]>C(OCC)C>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:16])[C:9]=1[N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH2:5][NH:6][C:18]([NH:17][C:20]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:21]=1[CH:22]=[CH:23][N:24]=[CH:25]2)=[O:19]

Participants

4

Reactant 2

HCID 115863575-IsocyanatoisoquinolineHCID 22337573581813-07-2

Product 1

HCID 10386145HCID 10386145, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The product from Example 177A (500 mg, 2.19 mmol) in diethyl ether (5 mL) was treated with an ethereal solution of 5-isocyanatoisoquinoline. The resulting waxy precipitate was collected by filtration and air-dried to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ 9.27 (s, 1H), 8.79 (s, 1H), 8.54 (d, 1H, J=6.1 Hz), 8.26 (dd, 1H, J=7.8 Hz, 1.0 Hz), 7.94 (d, 1H, 6.1 Hz), 7.76 (d, 1H, 8.2 Hz), 7.60 (t, 3H, J=7.6 Hz), 7.10 (t, 1H, J=6.0 Hz), 7.03 (m, 2H), 4.31 (d, 2H), 3.68 (m, 4H), 3.07 (m, 4H); MS (ESI+) m/z 399 (M+H).

Workup

  1. filtrationThe resulting waxy precipitate was collected by filtration
  2. customair-dried

Sources & evidence

ORD record
ord-f6ccd5f10058413cb64b092c8ae5ccbe
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

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