Triethylamine → HCID 59592956, compound

HRID 2262077Notes

Reaction equation

HRID 2262077 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:13]4[S:18][C:17]([CH:19]([CH3:23])C(O)=O)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[C:30](N1C=CN=C1)([N:32]1[CH:36]=CN=[CH:33]1)=[O:31].C(N(CC)CC)C.Cl.CNC>CN(C=O)C>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:24]4[CH2:25][CH2:26][O:27][CH2:28][CH2:29]4)[C:13]4[S:18][C:17]([CH2:19][CH2:23][C:30]([N:32]([CH3:36])[CH3:33])=[O:31])=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 86618385HCID 86618385, compound

Product 1

HCID 59592956HCID 59592956, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(1H-indazol-4-yl-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-yl]-propionic acid (145 mg) in DMF (5 mL) at room temperature was added carbonyldiimidazole (115 mg). The reaction mixture was then stirred at room temperature for 1 h. Then, triethylamine (0.15 mL) and dimethylamine hydrochloride (58 mg) were added and the solution was stirred at room temperature for 16 h. The reaction was then quenched with water (20 mL) and extracted into ethyl acetate (2×20 mL). The combined organics were washed with aqueous brine solution (3×20 mL), dried (MgSO4), concentrated and purified using column chromatography to give 148 as a white solid (96 mg). NMR: DMSO: 2.68-2.84 (2 H, m, CH2), 2.86 (3 H, s, Me), 3.02 (3 H, s, Me), 3.18 (2 H, t, J 7.22, CH2), 3.79-3.84 (4 H, m, CH2), 3.98-4.02 (4 H, m, CH2), 7.40 (1 H, s, Ar), 7.44 (1 H, t, J 8.0, Ar), 7.62 (1 H, d, J 8.15, Ar), 8.21 (1 H, d, J 7.35, Ar), 8.85 (1 H, s, Ar) and 13.15 (1 H, s, NH). MS: (ESI+): MH+ 437.22

Workup

  1. stirringthe solution was stirred at room temperature for 16 h
  2. customThe reaction was then quenched with water (20 mL)
  3. extractionextracted into ethyl acetate (2×20 mL)
  4. washThe combined organics were washed with aqueous brine solution (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-be523fb39db147aabd3a19158d89db89
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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