Triethylamine → N-(3-(Benzyloxy)-5-bromopyridin-2-yl)-4,5-dimethylthiazol-2-amine hydrochloride

HRID 1426171Notes

Reaction equation

HRID 1426171 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]([NH2:19])=[S:18])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][CH:21]([CH3:25])[C:22](=O)[CH3:23].C(N(CC)CC)C>C(O)C>[ClH:20].[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][C:21]([CH3:25])=[C:22]([CH3:23])[N:19]=2)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 200263-Chloro-2-butanoneHCID 727056401-(3-(Benzyloxy)-5-bromopyridin-2-yl)thiourea

Product 1

HCID 86639703N-(3-(Benzyloxy)-5-bromopyridin-2-yl)-4,5-dimethylthiazol-2-amine hydrochlorideYield 16.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-(benzyloxy)-5-bromopyridin-2-yl)thiourea (0.50 g, 1.48 mmol), 3-chlorobutan-2-one (0.236 g, 2.22 mmol), triethylamine (0.412 ml, 2.96 mmol), and ethanol (15 mL) was heated overnight. The reaction mixture was cooled, partitioned between ethyl acetate and water, washed with water and brine, dried, and concentrated. The residue was purified by MPLC eluting with 5:1 hexane:ethyl acetate to afford the free base of the title compound (104 mg) as a tacky oil. The free base was dissolved in ether (4 mL) and a 1M solution of HCl in ether was added (1.5 mL). The mixture was stirred 10 minutes and filtered. The solids were washed with ether, hexanes, and dried to afford 3-(benzyloxy)-5-bromo-N-(4,5-dimethylthiazol-2-ylpyridin-2-amine hydrochloride (0.093 g, 14.7% yield). 1H NMR (DMSO-d6) δ 2.21 (s, 3H), 2.26 (s, 3H), 5.34 (s, 2H), 7.35-7.44 (m, 3H), 7.58 (d, 2H), 7.81 (s, 1H), 8.05 (s, 1H).

Workup

  1. temperaturewas heated overnight
  2. temperatureThe reaction mixture was cooled
  3. custompartitioned between ethyl acetate and water
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by MPLC
  8. washeluting with 5:1 hexane

Sources & evidence

ORD record
ord-1ecc2a17e2d94d18807df85850ef9aaf
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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