Triethylamine → HCID 59593040, compound

HRID 2262279Notes

Reaction equation

HRID 2262279 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.[CH3:28][S:29](Cl)(=[O:31])=[O:30].CC1(C)C(C)(C)OB([C:41]2[CH:49]=[CH:48][CH:47]=[C:46]3[C:42]=2[CH:43]=[N:44][NH:45]3)O1>C(Cl)Cl>[NH:45]1[C:46]2[C:42](=[C:41]([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][S:29]([CH3:28])(=[O:31])=[O:30])([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:49]=[CH:48][CH:47]=2)[CH:43]=[N:44]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59592865HCID 59592865, compound

Product 1

HCID 59593040HCID 59593040, 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 (400 mg, 1.3 mmol) in CH2Cl2 (20 mL) was added Et3N (630 μL, 4.5 mmol) and methanesulfonyl chloride (200 μL, 2.6 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. The crude material was purified by silica gel chromatography (0-100% EtOAc in hexane). A portion (0.1 mmol) of the resulting pure 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 398 after reverse phase HPLC purification (8 mg). MS (Q1) 473 (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
  7. customThe crude material was purified by silica gel chromatography (0-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-1795b0ee18534f73b535cc28d08b309e
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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