3-Thiophenacetic acid → N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(3-thienyl)acetamide

HRID 1157594Notes

Reaction equation

HRID 1157594 reaction equation
O1C(C2C=C(N[C:13]3[N:18]=[C:17]([C:19]4[C:20]([C:28]5[CH:29]=[C:30]([NH:34][C:35](=[O:42])[CH2:36]C6SC=CC=6)[CH:31]=[CH:32][CH:33]=5)=[N:21][N:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=45)[CH:16]=[CH:15][N:14]=3)C=CC=2)=CN=C1.[S:43]1[CH:47]=[CH:46][C:45](CC(O)=O)=[CH:44]1.[ClH:52].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>C1COCC1.C(Cl)Cl>[Cl:52][C:13]1[N:18]=[C:17]([C:19]2[C:20]([C:28]3[CH:29]=[C:30]([NH:34][C:35](=[O:42])[CH2:36][C:45]4[CH:46]=[CH:47][S:43][CH:44]=4)[CH:31]=[CH:32][CH:33]=3)=[N:21][N:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=23)[CH:16]=[CH:15][N:14]=1

Participants

8

Reactant 5

HCID 234043-Thiophenacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57737194N-{3-[3-(2-{[3-(1,3-Oxazol-5-yl)phenyl]amino}-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(2-thienyl)acetamide

Product 1

HCID 57737204N-{3-[3-(2-Chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2-(3-thienyl)acetamideYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To solution of {3-[3-(2-chloro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}amine (125 mg, 0.4 mmol) (see Example 2, step A) in THF (5 mL) were added 3-thienylacetic acid (67 mg, 0.47 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (90 mg, 0.47 mmol), N-hydroxybenzotriazole (63 mg, 0.47 mmol), and diisopropylethylamine (200 μL, 1.2 mmol). After 20 h at rt, the reaction mixture was diluted with DCM, washed with water, dried over Na2SO4, filtered, and adsorbed onto silica gel. The crude product was purified by column chromatography to generate the title compound in 69% yield. ES-LC/MS m/z=446 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-57d54cc96eba45eab8a7b71168b1ada2
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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