Hydrochloric Acid → 3-[6-(5-Phenyl-thiazol-2-ylamino)-pyridin-3-yl]-propan-1-ol

HRID 1355503Notes

Reaction equation

HRID 1355503 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([NH2:14])=[S:13])=[N:9][CH:10]=1.Br[CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17](OC)OC.Cl.C([O-])([O-])=O.[Na+].[Na+]>CCO.O>[C:22]1([C:16]2[S:13][C:12]([NH:11][C:8]3[N:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=3)=[N:14][CH:17]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 11064658(1-Bromo-2,2-dimethoxyethyl)benzeneHCID 18506785[5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea

Product 1

HCID 185067863-[6-(5-Phenyl-thiazol-2-ylamino)-pyridin-3-yl]-propan-1-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

[5-(3-Hydroxy-propyl)-pyridin-2-yl]-thiourea (7-4), 2.20 g (10.4 mmol) was stirred in 20 mL EtOH. (1-Bromo-2,2-dimethoxy-ethyl)-benzene (3.83 g, 15.6 mmol) was added, dissolved in 12 mL EtOH. The reaction was heated to reflux. After 30 min, 8 mL of concentrated HCl (aq) was added. After 7 h the reaction was cooled to RT, and diluted with water. Na2CO3 (s) was added to pH 9. The resulting precipitate was filtered, and washed with water. To solid was added ether, the mixture was sonicated and filtered, washing with ether. Afford the titled compound as a white solid. 1H NMR (CDCl3): δ 8.74 (bs, 1H), 8.25 (d, 1H, J=2.2 Hz), 7.57 (dd, 2H, J=1.7, 9.0 Hz)7.49 (dd, 1H, J=2.4, 8.4 Hz), 7.38 (t, 2H, J=7.7 Hz), 6.83 (d, 1H, J=8.2 Hz), 3.71 (m, 2H), 2.70 (t, 2H, J=6.7 Hz), 1.89 (m, 2H). Mp 153-154° C. MS [M+H]+=312.2.

Workup

  1. temperatureThe reaction was heated to reflux
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. additionTo solid was added ether
  5. customthe mixture was sonicated
  6. filtrationfiltered
  7. washwashing with ether

Sources & evidence

ORD record
ord-961830be676f476282f78f8fe81743fd
Source dataset
uspto-grants-2003_07
Patent number
US06586424B2

Reaction notes

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