Ethyl Acetate → HCID 86618385, compound

HRID 2262076Notes

Reaction equation

HRID 2262076 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:5]2[S:10][C:9]([CH2:11][CH2:12]C(O)=O)=[CH:8][C:6]=2[N:7]=1.CC1(C)C(C)(C)OB([C:30]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:31]=2[CH:32]=[N:33][NH:34]3)O1.[C:40](=O)([O-:42])[O-:41].[Na+].[Na+].C(OCC)(=O)C>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH:34]1[C:35]2[C:31](=[C:30]([C:2]3[N:3]=[C:4]([N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)[C:5]4[S:10][C:9]([CH:11]([CH3:12])[C:40]([OH:42])=[O:41])=[CH:8][C:6]=4[N:7]=3)[CH:38]=[CH:37][CH:36]=2)[CH:32]=[N:33]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 454801864-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazoleHCID 86618384HCID 86618384, compound

Product 1

HCID 86618385HCID 86618385, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl)-propionic acid (200 mg), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indazole (209 mg), 1 M aqueous sodium carbonate solution (1.83 mL) and PdCl2(PPh3)2 (22 mg) in acetonitrile (3 mL) was reacted in the microwave at 140° C. for 15 min. The reaction mixture was then poured into a mixture of ethyl acetate (20 mL) and water (20 mL). The aqueous layer was collected and carefully acidified to pH 6 using 2 M aqueous hydrochloric acid. The product was then filtered and washed with water to give 3-[2-(1H-indazol-4-yl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl]-propionic acid as a grey solid (145 mg).

Workup

  1. customwas reacted in the microwave at 140° C. for 15 min
  2. customThe aqueous layer was collected
  3. filtrationThe product was then filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-e1a5dcff2700415181f9f32bc60996d2
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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