Benzeneacetic acid, 4-ethoxy- → HCID 22181344, compound

HRID 1796472Notes

Reaction equation

HRID 1796472 reaction equation
C1(C[N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:21][C:22]2[CH:23]=[N:24][C:25](OCC)=[CH:26]C=2)CC1.[CH2:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][C:41](O)=O)=[CH:36][CH:35]=1)[CH3:32].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.NC1C=C(C=CC=1NCC1C=CN=CC=1)C(N(CC)CC)=O>>[CH2:31]([O:33][C:34]1[CH:35]=[CH:36][C:37]([CH2:40][C:41]2[N:5]([CH2:6][C:21]3[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=3)[C:9]3[CH:10]=[CH:11][C:12]([C:14]([N:16]([CH2:17][CH3:18])[CH2:19][CH3:20])=[O:15])=[CH:13][C:8]=3[N:7]=2)=[CH:38][CH:39]=1)[CH3:32]

Participants

6

Reactant 5

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 10294778HCID 10294778, compoundHCID 22181353HCID 22181353, compound

Product 1

HCID 22181344HCID 22181344, compoundYield 36%

Procedure

Following general 13B, (4-ethoxyphenyl)acetic acid (0.0364 g, 0.202 mmol), HATU (0.0768 g, 0.202 mmol), DIPEA (0.048 mL, 0.28 mmol), and 3-amino-N,N-diethyl-4-[(4-pyridinylmethyl)amino]benzamide (0.0548 g, 0.184 mmol) were combined. The crude product was purified by reverse phase MPLC (gradient 10–50% CH3CN in H2O) to provide the title compound (0.0459 g, 36%) as its TFA salt. This material was lyophilized from H2O/dioxane to produce a white solid. 1H-NMR (CD3OD): δ 8.60 (br s, 2H), 7.87 (s, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.52 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 7.42 (d, J=5.6 Hz, 2H), 7.13 (d, J=8.4 Hz, 2H), 6.71 (d, J=9.6 Hz, 2H), 6.06 (s, 2H), 4.54 (s, 2H), 3.93 (q, J=7.2 Hz, 2H), 3.59 (br s, 2H), 3.31 (br s, 2H), 1.35 (t, J=6.8 Hz, 3H), 1.38–1.04 (2×br s, 6H). MS (ESI) (M+H)+443. Anal. Calcd for C27H30N4O2.2.1 TFA. 0.8H2O: C, 53.81; H, 4.88; N, 8.04. Found: C, 53.74; H, 4.89; N, 8.07.

Workup

  1. customThe crude product was purified by reverse phase MPLC (gradient 10–50% CH3CN in H2O)

Sources & evidence

ORD record
ord-f3b7a2a5aced41fba4ed195dffe92358
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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