1,3-Difluoro-5-isocyanatobenzene → HCID 86713661, compound

HRID 1430516Notes

Reaction equation

HRID 1430516 reaction equation
[NH2:1][C:2]1[C:3]([F:33])=[CH:4][C:5]([F:32])=[C:6]([C:8]2[C:9](=[O:31])[N:10]([CH2:29][CH3:30])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([N:18]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH3:19])[CH:12]=3)[CH:7]=1.[F:34][C:35]1[CH:36]=[C:37]([N:42]=[C:43]=[O:44])[CH:38]=[C:39]([F:41])[CH:40]=1>O1CCOCC1>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:18]([CH3:19])[C:13]2[N:14]=[CH:15][CH:16]3[CH:11]([CH:12]=2)[N:10]([CH2:29][CH3:30])[C:9](=[O:31])[C:8]([C:6]2[C:5]([F:32])=[CH:4][C:3]([F:33])=[C:2]([NH:1][C:43]([NH:42][C:37]4[CH:38]=[C:39]([F:41])[CH:40]=[C:35]([F:34])[CH:36]=4)=[O:44])[CH:7]=2)=[CH:17]3)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 27792821,3-Difluoro-5-isocyanatobenzene2×HCID 89611458HCID 89611458, compound

Product 1

HCID 86713661HCID 86713661, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of Example A7 (0.12 g, 0.266 mmol) in dioxane (5 mL) was treated with 3,5-difluorophenyl isocyanate (0.038 mL, 0.320 mmol) and stirred at RT overnight. Additional 3,5-difluorophenyl isocyanate (0.038 mL, 0.320 mmol) was added and the mixture stirred for 4 h. The resulting precipitate was collected via filtration and dried to yield 1-(5-(7-((4-methoxybenzyl)(methyl)amino)-1-ethyl-2-oxo-1,2,4a,8a-tetrahydro-1,6-naphthyridin-3-yl)-2,4-difluorophenyl)-3-(3,5-difluorophenyl)urea (112 mg, 69% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.38 (s, 1H), 8.67 (s, 1H), 8.52 (s, 1H), 8.05 (t, 1H), 7.86 (s, 1H), 7.38 (t, 1H), 7.19-7.14 (m, 4H), 6.86 (d, 2H), 6.80-6.77 (m, 1H), 6.32 (s, 1H), 4.85 (s, 2H), 4.19 (q, 2H), 3.70 (s, 3H), 3.12 (s, 3H), 1.13 (t, 3H); MS (ESI) m/z: 606.3 [M+H]+.

Workup

  1. stirringthe mixture stirred for 4 h
  2. filtrationThe resulting precipitate was collected via filtration
  3. customdried

Sources & evidence

ORD record
ord-9a879b6efabe42beb5f760045bd506ee
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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