1,2,3,4-Tetrahydroisoquinoline → HCID 86700212, compound

HRID 879405Notes

Reaction equation

HRID 879405 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21]CC)=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.CN(C)C(=O)C.[CH2:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39][CH2:38][NH:37]1.[OH-].[Na+]>CCO.C1COCC1>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([N:37]3[CH2:38][CH2:39][C:40]4[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:36]3)[S:3][C:4]=2[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=1)[C:19]([OH:21])=[O:20])([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 14798Sodium HydroxideHCID 31374DimethylacetamideHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700212HCID 86700212, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A vial was charged with (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (25 mg, 50 μmol), N,N-dimethylacetamide and 1,2,3,4-tetrahydroisoquinoline (50 μL). The reaction was heated to 100° C. for 30 min. Then THF (1 mL), EtOH (absolute, 500 μL), and 5 M aq NaOH (500 μL) were introduced. The reaction was heated for another 30 min at 100° C. The reaction was cooled to 23° C., and filtered (0.45 micron teflon syringe filter). The filtrate was purified by reverse phase HPLC, eluting by 5-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+: calc'd for C29H29ClN2O3S: 521.2, 523.2 (M+H+); Found: 521.2, 523.2 (M+H+). 1H NMR (400 MHz, CD3OD): δ 7.71-7.47 (m, 4H), 7.38 (s, 1H), 7.30-7.22 (m, 4H), 5.17 (s, 1H), 4.79 (s, 2H), 3.84 (t, J=6.0 Hz, 2H), 3.09 (t, J=6.0 Hz, 2H), 2.54 (s, 3H), 0.96 (s, 9H).

Workup

  1. temperatureThe reaction was heated for another 30 min at 100° C
  2. temperatureThe reaction was cooled to 23° C.
  3. filtrationfiltered
  4. filtration(0.45 micron teflon syringe filter)
  5. customThe filtrate was purified by reverse phase HPLC
  6. washeluting by 5-100% acetonitrile in H2O with 0.1% TFA

Sources & evidence

ORD record
ord-01d488030bc5437a9ff0eddaf7419d6a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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