Water → HCID 90414070, compound

HRID 1521994Notes

Reaction equation

HRID 1521994 reaction equation
[Cl:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([CH2:17]C)[CH2:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1.C([N:30]([CH2:33]C)CC)C.CNC(=O)[O:38]N1C(=O)CCC1=O.O>CN(C)C=O>[Cl:1][C:2]1[C:3]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[O:26][CH3:27])=[C:4]2[CH:10]=[C:9]([C:11]3[CH2:12][CH2:13][N:14]([C:17]([NH:30][CH3:33])=[O:38])[CH2:15][CH:16]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 43819351-[(Methylcarbamoyl)oxy]pyrrolidine-2,5-dioneHCID 90412344HCID 90412344, compound

Product 1

HCID 90414070HCID 90414070, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 229F (0.049 g, 0.137 mmol) and triethylamine (0.057 mL, 0.411 mmol) in N,N-dimethylformamide (1.4 mL) was treated with 2,5-dioxopyrrolidin-1-yl methylcarbamate (0.035 g, 0.205 mmol) and the mixture was stirred at room temperature for 16 hours. The mixture was poured into water and the solid was filtered and dried under vacuum to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ 2.32-2.43 (m, 2H), 2.58 (d, J=4.3 Hz, 3H), 3.46 (t, J=5.7 Hz, 2H), 3.70 (s, 3H), 3.96-4.03 (m, 2H), 6.01-6.08 (m, 1H), 6.40-6.47 (m, 1H), 6.47-6.55 (m, 1H), 7.14 (dd, J=8.6, 3.1 Hz, 1H), 7.20 (dd, J=9.2, 4.5 Hz, 1H), 7.26-7.39 (m, 1H), 8.24 (s, 1H), 12.03 (bs, 1H). MS (ESI+) m/z 415.1 (M+H)+.

Workup

  1. filtrationthe solid was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-a69f61276a854706b38aed5a4408e265
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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