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Triethylamine → HCID 59593030, compound

HRID 2262290
Notes
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Reaction equation

HRID 2262290 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:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1.CC1(C)C(C)(C)OB([C:46]2[CH:54]=[CH:53][CH:52]=[C:51]3[C:47]=2[CH:48]=[N:49][NH:50]3)O1>C(Cl)Cl>[NH:50]1[C:51]2[C:47](=[C:46]([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:36])[C:30]5[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=5)([CH3:13])[CH3:12])=[CH:8][C:6]=4[N:7]=3)[CH:54]=[CH:53][CH:52]=2)[CH:48]=[N:49]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 59592865HCID 59592865, compound

Product 1

HCID 59593030HCID 59593030, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

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 (450 μL, 3.2 mmol) and nicotinoyl chloride hydrochloric acid (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 410 after reverse phase HPLC purification (22 mg). MS (Q1) 500 (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-5fcb12be65dc4d56b7120bd2da7c62ea
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846929B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes