m-Anisoyl chloride → HCID 59736821, compound

HRID 252837Notes

Reaction equation

HRID 252837 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH2:12][C:13]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][C:14]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:12][C:13]1[CH:18]=[C:17]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:15][C:14]=1[NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:7]

Participants

4

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 57717474tert-Butyl (2-amino-4-(thiophen-2-yl)phenyl)carbamate

Product 1

HCID 59736821HCID 59736821, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Methoxybenzoyl chloride 179 (0.20 g, 1.17 mmol) and 178 (0.34 g, 1.17 mmol) were stirred in pyridine (15 mL) at rt for 4 hrs then the pyridine was removed by rotary evaporation and the crude material was purified by column chromatography (25% ethyl acetate in hexanes) to provide the title compound 180 (0.44 g, 89% yield). 1H NMR: (DMSO) δ (ppm): 400 MHz, (DMSO) d (ppm): 9.88 (s, 1H), 8.72 (s, 1H), 7.80 (s, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.43 to 7.55 (m, 6H), 7.17 (dd, J=7.6, 1.8 Hz, 1H), 7.11 (dd, J=4.9, 3.5 Hz, 1H), 3.84 (s, 3H), 1.46 (s, 9H). MS: (calc.) 424.15; (obt.) 425.1 (MH)+.

Workup

  1. customthe pyridine was removed by rotary evaporation
  2. customthe crude material was purified by column chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-80c6add280e34eecb05f64db8a829f23
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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