Hydrochloric Acid → HCID 59593151, compound

HRID 2098863Notes

Reaction equation

HRID 2098863 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:5]2[S:10][C:9]([C:11]([NH2:14])([CH3:13])[CH3:12])=[CH:8][C:6]=2[N:7]=1.CCN(CC)CC.Cl.[C:29](Cl)(=[O:38])[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1.CC1(C)C(C)(C)OB([C:48]2[CH:56]=[CH:55][CH:54]=[C:53]3[C:49]=2[CH:50]=[N:51][NH:52]3)O1>C(Cl)Cl>[NH:52]1[C:53]2[C:49](=[C:48]([C:2]3[N:3]=[C:4]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[C:5]4[S:10][C:9]([C:11]([NH:14][C:29](=[O:38])[C:30]5[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=5)([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:56]=[CH:55][CH:54]=2)[CH:50]=[N:51]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59592865HCID 59592865, compound

Product 1

HCID 59593151HCID 59593151, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)propan-2-amine (150 mg, 0.5 mmol) in CH2Cl2 (10 mL) was added Et3N (230 μL, 1.6 mmol) and the HCl salt of p-anisoyl chloride (160 mg, 0.9 mmol). The resulting mixture stirred at room temperature overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. A portion (0.2 mmol) of the resulting crude material was utilized in a Suzuki coupling using General Procedure A with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole 7 to provide 412 after reverse phase HPLC purification (30 mg). MS (Q1) 529 (M)+

Workup

  1. customThe reaction was quenched by the addition of saturated aqueous NaHCO3
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e98f05f5d0f4ec495aae752ec94f537
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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