Hydrochloric Acid → HCID 71060759, compound

HRID 529041Notes

Reaction equation

HRID 529041 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:29]([C:30]([O:32]CC)=[O:31])=[CH:28][N:27]=[C:26]([N:35]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[N:25]=4)=[C:20]([C:44]([N:46]4[CH2:55][CH2:54][C:53]5[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=5)[CH2:47]4)=[O:45])[CH:19]=3)=[O:17])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH:15][C:16]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:29]([C:30]([OH:32])=[O:31])=[CH:28][N:27]=[C:26]([N:35]([CH2:40][CH2:41][CH2:42][CH3:43])[CH2:36][CH2:37][CH2:38][CH3:39])[N:25]=4)=[C:20]([C:44]([N:46]4[CH2:55][CH2:54][C:53]5[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=5)[CH2:47]4)=[O:45])[CH:19]=3)=[O:17])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71060821HCID 71060821, compound

Product 1

HCID 71060759HCID 71060759, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of ethyl 4-(4-(7-chloronaphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-2-(dibutylamino)pyrimidine-5-carboxylate (Example 319, 23 mg, 0.03 mmol) in THF (1.0 mL) and MeOH (1.0 mL) was added 2N NaOH (0.15 mL, 0.30 mmol). The resulting reaction mixture was stirred at 55° C. for 3 h. At 0° C., the reaction mixture was neutralized to pH 3-4 with aq. 1N HCl. The solution was extracted with EtOAc (3×) and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (14 mg, 63%). MS(ESI+) m/z 754.3 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. customAt 0° C.
  3. extractionThe solution was extracted with EtOAc (3×)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-b182f2fb32ef4d94bef63495e21138a5
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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