Potassium Carbonate → HCID 86700327, compound

HRID 879506Notes

Reaction equation

HRID 879506 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]3[CH2:16][NH:15][CH2:14][CH2:13][N:12]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Br[C:25]1[S:26][C:27]2[C:33]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[C:32]([C@H:41]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])[C:42]([O:44][CH2:45][CH3:46])=[O:43])[C:31]([CH3:52])=[CH:30][C:28]=2[N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:48]([O:47][C@@H:41]([C:32]1[C:31]([CH3:52])=[CH:30][C:28]2[N:29]=[C:25]([N:15]3[CH2:14][CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]([C:7]4[CH:6]=[C:5]5[C:10](=[CH:9][CH:8]=4)[N:2]([CH3:1])[N:3]=[CH:4]5)[CH2:16]3)[S:26][C:27]=2[C:33]=1[C:34]1[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=1)[C:42]([O:44][CH2:45][CH3:46])=[O:43])([CH3:49])([CH3:50])[CH3:51]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetateHCID 86700326HCID 86700326, compound

Product 1

HCID 86700327HCID 86700327, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

The mixture of tert-butyl 2-(1-methyl-1H-indazol-5-yl)piperazine-1-carboxylate (10 mg, 0.03 mmol), (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (15 mg, 0.03 mmol), and potassium carbonate (41 mg, 0.3 mmol) in DMF (0.5 mL) was heated at 140° C. for 4 hours. The mixture was cooled, and was quenched with water. The mixture was extracted with ethyl acetate, and the organic phase was washed with water and brine, and was dried with sodium sulfate. Concentration and purification by reverse phase HPLC gave tert-butyl 4-(6-((S)-1-tert-butoxy-2-ethoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)-2-(1-methyl-1H-indazol-5-yl)piperazine-1-carboxylate. LCMS-ESI+: calc'd for C39H47ClN5O5S2: 732.3 (M+H+); Found: 732.2 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. customwas quenched with water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic phase was washed with water and brine
  5. dry with materialwas dried with sodium sulfate
  6. concentrationConcentration and purification by reverse phase HPLC

Sources & evidence

ORD record
ord-119fb95a63b54147a4ae360fb605a223
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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