Hydrochloric Acid → 6-(6-Chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine

HRID 2077534Notes

Reaction equation

HRID 2077534 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15]C(=O)C)[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:21][CH:22]([CH3:24])[CH3:23].[OH-].[Na+].O.Cl>CO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:21][CH:22]([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 57585083N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 575849166-(6-Chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amineYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

N-(6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (123.6 mg, 342.5 μmol) was suspended in MeOH (2.2 ml) and sodium hydroxide (89.90 mg, 2248 μmol) and water (0.44 ml) were added. The reaction flask was fit with a reflux condenser and placed in a preheated oil bath (80° C.), and the reaction was stirred for 1 hour. The reaction was cooled to room temperature, treated with 5 N HCl to neutralize the solution, and allowed to stand overnight. It was then extracted with 10:1 DCM/MeOH, and the organic extracts were combined, concentrated, and purified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH). Fractions with product collected, concentrated, and treated with Et2O and MeOH. The MeOH washings were decanted, and the solid was collected and dried under high vacuum to afford 6-(6-chloro-5-(isopropylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (18.2 mg, 17% yield). MS (ESI pos. ion) m/z: 319. Calculated exact mass for C15H15ClN4S 318.

Workup

  1. customThe reaction flask was fit with a reflux condenser
  2. customplaced in a preheated oil bath
  3. temperatureThe reaction was cooled to room temperature
  4. waitto stand overnight
  5. extractionIt was then extracted with 10:1 DCM/MeOH
  6. concentrationconcentrated
  7. custompurified on a silica gel column (20:1 DCM/MeOH to 15:1 DCM/2 N ammonia in MeOH)
  8. customFractions with product collected
  9. concentrationconcentrated
  10. additiontreated with Et2O and MeOH
  11. customThe MeOH washings were decanted
  12. customthe solid was collected
  13. customdried under high vacuum

Sources & evidence

ORD record
ord-b37fecfcdbcc4b81986200b8529c81d4
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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