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

HRID 879598Notes

Reaction equation

HRID 879598 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].[CH3:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.O1CCO[CH2:46][CH2:45]1>>[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:41]4[CH2:42][CH2:43][N:38]([CH:37]([CH2:45][CH3:46])[CH2:36][CH3:35])[CH2:39][CH2:40]4)[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])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 3

HCID 312751,4-DioxaneHCID 415812Piperazine, 1-propyl-, hydrochloride (1:2)HCID 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 86700413(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(4-(pentan-3-yl)piperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

Procedure

To (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-chloropyrimidin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate (40.0 mg, 0.077 mmol) was added 1-(3-propyl)-piperazine (60.5 mg, 0.387 mmol) in 1,4-dioxane (1 mL). The reaction mixture was stirred at room temperature for 20 min, then 40° C. for 1 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 C34H43ClN5O3S (M+H+): 636.3; Found: 636.2 (M+H+).

Workup

  1. wait40° C. for 1 h
  2. customUpon completion of the reaction
  3. filtrationthe reaction mixture was filtered through Celite (ethyl acetate eluent)
  4. concentrationconcentrated
  5. customused without further purification

Sources & evidence

ORD record
ord-0bd904c5b2a9405aabba2b4fc8999583
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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