Benzeneacetic acid, 4-ethoxy- → HCID 22181304, compound

HRID 1796470Notes

Reaction equation

HRID 1796470 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](O)=O)=[CH:6][CH:5]=1)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:47][C:48]1[CH:49]=[C:50]([CH:58]=[CH:59][C:60]=1[NH:61][CH2:62][CH2:63][CH:64]([CH3:66])[CH3:65])[C:51]([N:53]([CH2:56][CH3:57])[CH2:54][CH3:55])=[O:52]>>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[N:61]([CH2:62][CH2:63][CH:64]([CH3:66])[CH3:65])[C:60]3[CH:59]=[CH:58][C:50]([C:51]([N:53]([CH2:56][CH3:57])[CH2:54][CH3:55])=[O:52])=[CH:49][C:48]=3[N:47]=2)=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 4

HCID 78631Benzeneacetic acid, 4-ethoxy-HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22181315HCID 22181315, compound

Product 1

HCID 22181304HCID 22181304, compoundYield 90%

Procedure

Following general procedure 13B, (4-ethoxyphenyl)acetic acid (0.110 g, 0.612 mmol), HATU (0.233 g, 0.611 mmol), DIPEA (0.15 m, 0.86 mmol), and 3-amino-N,N-diethyl-4-(isopentylamino)benzamide (0.154 g, 0.556 mmol) were combined. The crude product was purified by column chromatography (19:1 CH2Cl2:MeOH) to provide the title compound (0.211 g, 90%). 1H-NMR (CD3OD): δ 7.67 (s, 1H), 7.50 (d, J=8.4 Hz, 1H), 7.30 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 7.16 (d, J=9.2 Hz, 2H), 6.86 (d, J=8.4 Hz, 2H), 4.28 (s, 2H), 4.12 (m, 2H), 3.98 (q, J=7.6 Hz, 2H), 3.57 (br s, 2H), 3.34 (br s, 2H), 1.62–1.48 (m, 1H), 1.34 (t, J=7.6 Hz, 3H), 1.36–1.07 (overlapping 2×br s and m, 8H), 0.88 (d, J=6.8 Hz, 6H). MS (ES) (M+H)+=422. Anal. Calcd for C26H35N3O2.1.7 TFA.0.2H2O: C, 57.05; H, 6.04; N, 6.79. Found: C, 57.11; H, 6.09; N, 6.69.

Workup

  1. customThe crude product was purified by column chromatography (19:1 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-2b155735838d4e4d80090f0f936ab745
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

Loading…