(4-Nitrophenyl)acetic acid → HCID 10248394, compound

HRID 1016672Notes

Reaction equation

C[CH2:2][N:3]=C=NCCCN(C)C.[CH3:12][CH2:13][N:14]([CH:18]([CH3:20])C)[CH:15]([CH3:17])C.[N+:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([OH:33])=O)=[CH:26][CH:25]=1)([O-:23])=[O:22].[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=N[C:38]=2[CH:39]=1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C>>[N+:21]([C:24]1[CH:25]=[CH:26][C:27]([CH2:30][C:31]([N:3]([CH3:2])[C@@H:20]([C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:18][N:14]2[CH2:13][CH2:12][CH2:17][CH2:15]2)=[O:33])=[CH:28][CH:29]=1)([O-:23])=[O:22]

Participants

Reactant 5

HCID 4661(4-Nitrophenyl)acetic acid

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 757711-Hydroxybenzotriazole

HCID 81531Diisopropylethylamine

HCID 86755171HCID 86755171, compound

Product 1

HCID 10248394HCID 10248394, compoundYield 93%

Procedure

ADL-01-0079-2 was prepared via the general EDCI/DIPEA coupling procedure from 28 (1.5 g; 7.3 mmol), 4-Nitrophenylacetic acid(2.0 g; 11.0 mmol), HOBT (1.4 g; 11 mmol), EDCI (2.1 g; 11.0mmol), and DIPEA (2.5 mL; 14.6 mmol). The crude product was purified by flash chromatography using a stepwise gradient of 1% to 5% MeOH: methylene chloride to afford 2.5 g(93%) of pure product which was treated with 1.0HCl in diethyl ether to give 39 as the HCl salt. 1H NMR(HCl salt, CDCl3) δ1.6(br, m, 4H, —CH2CH2—), 2.8(br, s, 3H, —NCH3), 6.4(br, m,1H, —CH), 7.1-7.5(complex, 7H, aromatic), 8.0(br, d, 2 h, aromatic). MS (FAB) m/z 367. Anal. (C,H,N) C21H25N3O3.HCl.

Workup

customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-c7345b01f26d4f53851d3095898400a5
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06476063B2

Reaction notes

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