Dimethylformamide → HCID 59592956, compound

HRID 2098656Notes

Reaction equation

HRID 2098656 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(N(CC)CC)C.Cl.CNC.[CH3:41][N:42]([CH:44]=[O:45])[CH3:43]>>[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:44]([N:42]([CH3:43])[CH3:41])=[O:45])=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 86618385HCID 86618385, compound

Product 1

HCID 59592956HCID 59592956, compound

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 carbonyliimidazole (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-4ddf6efdbc4045efa55b92178c4f737c
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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