1,4-Dioxane hydrochloride → 4-(2-(2-fluoroethylthio)benzo[d]thiazol-6-yl)-N-methylaniline

HRID 1965860Notes

Reaction equation

HRID 1965860 reaction equation
[F:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([N:20](C)[C:21](=O)OC(C)(C)C)=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1.O1CCOCC1.Cl>>[F:1][CH2:2][CH2:3][S:4][C:5]1[S:6][C:7]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([NH:20][CH3:21])=[CH:16][CH:15]=3)[CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59283015Tert-butyl 4-(2-(2-fluoroethylthio)benzo[d]thiazol-6-yl)phenyl(methyl)carbamate

Product 1

HCID 592829164-(2-(2-fluoroethylthio)benzo[d]thiazol-6-yl)-N-methylaniline

Procedure

Tert-butyl 4-(2-(2-fluoroethylthio)benzo[d]thiazol-6-yl)phenyl(methyl)carbamate (15 mg, 0.036 mmol) was treated with 3 mL of 4 M HCl dioxane solution for 2 h and concentrated. The crude product was purified with RP-HPLC (20% to 80% TFA buffered MeCN in water) to afford 4-(2-(2-fluoroethylthio)benzo[d]thiazol-6-yl)-N-methylaniline as a yellow wax (4 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 7.84 (d, J=8.4 Hz, 1 H), 7.81 (d, J=1.6 Hz, 1 H), 7.58-7.56 (m, 2 H), 7.53 (dd, J=8.8, 2.0 Hz, 1 H), 7.34-7.32 (m, 2 H), 4.86 (t, J=6.4 Hz, 11 H), 4.74 (t, J=6.4 Hz, 1 H), 3.73 (t, J=6.4 Hz, 1 H), 3.68 (t, J=6.4 Hz, 1 H), 3.02 (s, 3 H); MS (ESI) m/z 319 (M+H+).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified with RP-HPLC (20% to 80% TFA buffered MeCN in water)

Sources & evidence

ORD record
ord-1f6890f82d5f4c05a8bd0e34333f1662
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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