Benzoyl chloride → HCID 59592965, compound

HRID 2098845Notes

Reaction equation

HRID 2098845 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.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC1(C)C(C)(C)OB([C:45]2[CH:53]=[CH:52][CH:51]=[C:50]3[C:46]=2[CH:47]=[N:48][NH:49]3)O1>C(Cl)Cl.Cl>[NH:49]1[C:50]2[C:46](=[C:45]([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:28](=[O:35])[C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:53]=[CH:52][CH:51]=2)[CH:47]=[N:48]1

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59592865HCID 59592865, compound

Product 1

HCID 59592965HCID 59592965, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)propan-2-amine (1.1 g, 3.5 mmol) in CH2Cl2 (50 mL) was added Et3N (0.6 mL, 4.9 mmol) and benzoyl chloride (0.6 mL, 4.2 mmol). The resulting mixture stirred at room temperature overnight. The reaction was diluted with 1 M HCl and extracted with DCM, dried over MgSO4, and concentrated in vacuo. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexane). A portion (0.65 mmol) of the 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 388 after reverse phase HPLC purification (133 mg). MS (Q1) 499 (M)+

Workup

  1. extractionextracted with DCM
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexane)

Sources & evidence

ORD record
ord-a6eccc22f28f420fae5637751b3974dd
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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