Diethylamine → N,N-Diethyl-6-methoxy-9-oxo-9H-xanthene-3-carboxamide

HRID 733063Notes

Reaction equation

HRID 733063 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[C:12]1[CH:11]=[CH:10][C:9]([C:18](O)=[O:19])=[CH:8][C:7]=1[O:6]2.[CH:21]([N:24](CC)[CH:25](C)[CH3:26])(C)[CH3:22].C(NCC)C>CN(C)C=O>[CH2:21]([N:24]([CH2:25][CH3:26])[C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[O:17])[C:14]3[C:5]([O:6][C:7]=2[CH:8]=1)=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=3)=[O:19])[CH3:22]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 81531DiisopropylethylamineHCID 578391996-Methoxy-9-oxo-9H-xanthene-3-carboxylic acid

Product 1

HCID 57839204N,N-Diethyl-6-methoxy-9-oxo-9H-xanthene-3-carboxamideYield 52.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 6i (0.707 g, 2.62 mmol) and O-benzotriazol-yl-N,N,N′,N-tetramethyluronium hexafluorophosphate (HBTU, 1.05 g, 2.74 mmol) in N,N-dimethylformamide (10 mL) was treated with N,N-diisopropylethylamine (DIEA, 0.685 mL, 3.92 mmol) and allowed to stir at rt for 15 min. Diethylamine (0.541 mL, 5.23 mL) was added and the resultant mixture was stirred for 2 h. The mixture was poured into ice water. A solid was collected by filtration, washed with water and air dried to give the title compound (0.445 g). MS: m/z 326.0 (MH+). 1H NMR (DMSO-d6): δ 1.07 (br t, 3 H), 1.19 (br t, 3 H), 3.20 (br q, 2 H), 3.48 (br t, 2 H), 3.95 (s, 3 H), 7.08 (m, 1 H), 7.17 (d, 1 H, J=2.1 Hz), 7.40 (d of d, 1H, J=1.3 & 8.1 Hz), 7.59 (d, 1 H, J=1.2 Hz), 8.12 (d of d, 1 H, J=1.3 & 8.9 Hz) and 8.21 (d, 1 H, J=8.1 Hz).

Workup

  1. filtrationA solid was collected by filtration
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-cf70564edfab4b2194880c60283661be
Source dataset
uspto-grants-2009_09
Patent number
US07589103B2

Reaction notes

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