Hydrochloric Acid → (S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-((R)-3-methylpiperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

HRID 879615Notes

Reaction equation

HRID 879615 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:39]([CH3:40])=[CH:38][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[C@H:26]([CH3:37])[CH2:25]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:4])([CH3:3])[CH3:2].Cl>O1CCOCC1>[C:1]([O:5][C@@H:6]([C:11]1[C:39]([CH3:40])=[CH:38][C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([N:24]4[CH2:29][CH2:28][NH:27][C@H:26]([CH3:37])[CH2:25]4)[N:19]=3)[S:17][C:13]=2[C:12]=1[C:41]1[CH:42]=[CH:43][C:44]([Cl:47])=[CH:45][CH:46]=1)[C:7]([O:9][CH3:10])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86700422(R)-tert-butyl 4-(4-(6-((S)-1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)pyrimidin-2-yl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 86700423(S)-methyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-((R)-3-methylpiperazin-1-yl)pyrimidin-4-yl)benzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To crude (R)-tert-butyl 4-(4-(6-((S)-1-tert-butoxy-2-methoxy-2-oxoethyl)-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-2-yl)pyrimidin-2-yl)-2-methylpiperazine-1-carboxylate in 1,4-dioxane (1.25 mL) was added HCl (0.78 mL of a 4M solution in 1,4-dioxane). The reaction mixture was stirred at room temperature for 2.5 h then concentrated. The resulting solid was suspended in diethyl ether, concentrated and dried under high vacuum overnight. The resulting solid was taken up in water, basified with 2N NaOH, and extracted three times with DCM. The combined organic layers were dried over sodium sulfate, filtered, concentrated, and used without further purification. LCMS-ESI+ calc'd for C30H35ClN5O3S (M+H+): 580.2; Found: 580.2 (M+H+).

Workup

  1. concentrationthen concentrated
  2. concentrationconcentrated
  3. customdried under high vacuum overnight
  4. extractionextracted three times with DCM
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customused without further purification

Sources & evidence

ORD record
ord-076a96182ccb46cbaf7b95f60c305f92
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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