Hydrochloric Acid → 3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-methylamino-ethoxy)-benzamide, hydrochloride salt

HRID 2218482Notes

Reaction equation

HRID 2218482 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][O:11][NH:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[C:16]=1[NH:23][C:24]1[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=1[F:31])=[O:14])C)(C)(C)C.[ClH:33]>>[ClH:33].[F:22][C:17]1[C:16]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([I:30])=[CH:26][C:25]=2[F:31])=[C:15]([CH:20]=[CH:19][C:18]=1[F:21])[C:13]([NH:12][O:11][CH2:10][CH2:9][NH:7][CH3:6])=[O:14]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86591461[2-({1-[3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-phenyl]-methanoyl}-aminooxy)-ethyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 101640413,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-methylamino-ethoxy)-benzamide, hydrochloride saltYield 85%

Procedure

[2-({1-[3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-phenyl]-methanoyl}-aminooxy)-ethyl]-methyl-carbamic acid tert-butyl ester (3.28 g, 5.80 mmol) was dissolved in ethereal hydrogen chloride solution (20 mL, 1.0 M in diethyl ether). The resultant solution was stirred at ambient temperature for 48 h, during which precipitation of a white solid ensued. Hexanes (20 mL) was added and the reaction mixture was stirred vigorously for an additional 20 min. The reaction mixture was filtered, and the filter cake was broken up with a spatuala. The solid was washed with hexanes (50 mL) and ether (20 mL) and was dried in vacuo to afford a free-flowing, tan-colored powder (2.46 g, 85% yield). Recrystallization from acetonitrile afforded colorless needles: m.p. 173-176° C.; 1 H NMR (400 MHz, DMSO-d6) δ 12.27 (s, 1 H), 8.76 (br s, 2 H), 8.64 (s, 1 H), 7.55 (dd, J=11.0, 1.9 Hz, 1 H), 7.47 (dd, J=7.1, 6.3 Hz, 1 H), 7.33 (d, J=8.3 Hz, 1 H), 7.23 (dt, J=7.6, 9.2 Hz, 1 H), 6.64 (td, J=8.8, 4.2 Hz, 1 H), 4.05 (t, 4.9 Hz, 2 H), 3.11 (br s, 2 H), 2.56 (t, J=4.6 Hz, 3 H); 19F NMR (376 MHz, DMSO-d6) δ −128.2 (t, J=10.1 Hz), −132.5 (d, J=20.2 Hz), −144.0 (d, 20.2 Hz). Anal Calcd./Found for C16H16F3IN3O2Cl: C, 38.31/38.20; H, 3.21/3.10; N, 8.38/8.34; F, 11.36/11.21; Cl, 7.07/7.05.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washThe solid was washed with hexanes (50 mL) and ether (20 mL)
  3. customwas dried in vacuo

Sources & evidence

ORD record
ord-525bc642507143538aae573458e72f06
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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