1-(Oxetan-3-yl)piperazine → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(4-(oxetan-3-yl)piperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879658Notes

Reaction equation

HRID 879658 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20](Cl)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].[O:35]1[CH2:38][CH:37]([N:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:36]1>O1CCOCC1>[C:1]([O:5][C@@H:6]([C:11]1[C:26]([CH3:27])=[CH:25][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:42]4[CH2:43][CH2:44][N:39]([CH:37]5[CH2:38][O:35][CH2:36]5)[CH2:40][CH2:41]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:28]1[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 574162871-(Oxetan-3-yl)piperazineHCID 86700414(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

Product 1

HCID 86700471(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(4-(oxetan-3-yl)piperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (49.0 mg, 0.095 mmol) was added 1-(oxetan-3-yl)piperazine (27.0 mg, 0.190 mmol) in 1,4-dioxane (1 mL). The reaction mixture was stirred at room temperature for 6 h. Upon completion of the reaction, the reaction mixture was filtered through Celite (ethyl acetate eluent), concentrated, and used without further purification. LCMS-ESI+ calc'd for C32H37ClN5O4S (M+H+): 622.2; Found: 622.2 (M+H+).

Workup

  1. customUpon completion of the reaction
  2. filtrationthe reaction mixture was filtered through Celite (ethyl acetate eluent)
  3. concentrationconcentrated
  4. customused without further purification

Sources & evidence

ORD record
ord-30d0db471fbb4a18ab5c18bb557f21b3
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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