Triethylamine → HCID 59592941, compound

HRID 2262291Notes

Reaction equation

HRID 2262291 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:37])[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=1.CC1(C)C(C)(C)OB([C:47]2[CH:55]=[CH:54][CH:53]=[C:52]3[C:48]=2[CH:49]=[N:50][NH:51]3)O1>C(Cl)Cl>[NH:51]1[C:52]2[C:48](=[C:47]([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:37])[C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[CH:30]=5)([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:55]=[CH:54][CH:53]=2)[CH:49]=[N:50]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59592865HCID 59592865, compound

Product 1

HCID 59592941HCID 59592941, 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 m-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 product 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 411 after reverse phase HPLC purification (13 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-ce6a3ef08182455fa1e6aa7c870e37d7
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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