HCID 57633961, compound → 4-Chloro-5-(6-isoquinolinyl)-2-thiazolamine

HRID 661096Notes

Reaction equation

HRID 661096 reaction equation
COC1C=CC(C[N:8]([C:16]2[S:17][C:18]([C:22]3[CH:23]=[C:24]4[C:29](=[CH:30][CH:31]=3)[CH:28]=[N:27][CH:26]=[CH:25]4)=[C:19]([Cl:21])[N:20]=2)C(=O)OC(C)(C)C)=CC=1>CC(O)=O>[Cl:21][C:19]1[N:20]=[C:16]([NH2:8])[S:17][C:18]=1[C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[CH:28]=[N:27][CH:26]=[CH:25]2

Participants

3

Reactant 1

HCID 57633961HCID 57633961, compound

Product 1

HCID 576342064-Chloro-5-(6-isoquinolinyl)-2-thiazolamineYield 85.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A glass microwave reaction vessel was charged with tert-butyl 4-methoxybenzyl(4-chloro-5-(isoquinolin-6-yl)thiazol-2-yl)carbamate (1.5 g, 3.12 mmol) and AcOH. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc.,) at 120° C. for 5 minutes. Excess AcOH was removed under high vacuum. The residue was dissolved in DCM and washed with saturated NaHCO3 (50 mL) and saturated sodium chloride. This intermediate was synthesized in the same manner as described previously and water dried over Na2SO4, filtered and concentrated in vacuo to provide 4-chloro-5-(isoquinolin-6-yl)thiazol-2-amine (0.7 g, 81% yield), m/z (%): 263.2 (100%, M++H).

Workup

  1. customA glass microwave reaction vessel
  2. customExcess AcOH was removed under high vacuum
  3. dissolutionThe residue was dissolved in DCM
  4. washwashed with saturated NaHCO3 (50 mL) and saturated sodium chloride
  5. customThis intermediate was synthesized in the same manner
  6. dry with materialwater dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d81f63509f31478db68caaf75195342e
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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