Hydrochloric Acid → HCID 59593151, compound

HRID 2262292Notes

Reaction equation

HRID 2262292 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-7f299bcf96ec4fb68fd16d87ccbb7d02
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

Loading…