1,4-Dioxane hydrochloride → N-(2-fluoroethyl)-6-(4-(methylamino)phenyl)benzo[d]thiazol-2-amine hydrochloride

HRID 1965856Notes

Reaction equation

HRID 1965856 reaction equation
[F:1][CH2:2][CH2:3][NH: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.[ClH:35]>>[ClH:35].[F:1][CH2:2][CH2:3][NH: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 59282872Tert-butyl 4-(2-(2-fluoroethylamino)benzo[d]thiazol-6-yl)phenyl(methyl)carbamate

Product 1

HCID 86640940N-(2-fluoroethyl)-6-(4-(methylamino)phenyl)benzo[d]thiazol-2-amine hydrochlorideYield 74%

Procedure

Tert-butyl 4-(2-(2-fluoroethylamino)benzo[d]thiazol-6-yl)phenyl(methyl)carbamate (25 mg, 0.06 mmol) was treated with 4 mL of 4 M HCl dioxane solution for 2 h and concentrated. The residue was washed with ether (2×3 mL) and dried under high vacuum to afford N-(2-fluoroethyl)-6-(4-(methylamino)phenyl)benzo[d]thiazol-2-amine hydrochloride as a yellow solid (15 mg, 74%). 1H NMR (400 MHz, methanol-d4) δ 8.18 (s, 1 H), 7.91-7.88 (m, 2 H), 7.86-7.84 (m, 1 H), 7.67 (m, 3 H), 4.82 (t, J=4.8 Hz, 1 H), 4.70 (t, J=4/8 Hz, 1 H), 3.99 (t, J=4.4 Hz, 1 H), 3.93 (t, J=4.4 Hz, 1 H), 3.13 (s, 3 H); MS (ESI) m/z 302 (M+H+).

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with ether (2×3 mL)
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-be55c4b32c5940aa9497d667396f396c
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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