Pyridine → HCID 15958091, compound

HRID 270957Notes

Reaction equation

HRID 270957 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2C=C[C:18]3[N:19]([N:27]=[CH:28][C:29]=3[NH2:30])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:31]1C=CC=C[CH:32]=1.[CH:37]1([C:40](Cl)=[O:41])[CH2:39][CH2:38]1.[CH2:43]([S:45](Cl)(=[O:47])=[O:46])[CH3:44].[CH3:49][N:50](C1C=CC=CN=1)C>C(#N)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:32]=[N:31][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[NH:30][C:40]([CH:37]3[CH2:39][CH2:38]3)=[O:41])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:49]=[N:50][C:18]3[N:19]([N:27]=[CH:28][C:29]=3[NH:30][S:45]([CH2:43][CH3:44])(=[O:47])=[O:46])[C:20]=2[CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 218852-DimethylaminopyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 69312584HCID 69312584, compound

Product 2

HCID 10051263HCID 10051263, compoundYield 46%HCID 15958091HCID 15958091, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 30 mg (0.075 mmol) 6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyridin-3-ylamine in 2 mL of acetonitrile (CH3CN) was added 0.018 mL (0.225 mmol) of pyridine (pyr), followed by 16 mg (0.2 mmol) of cyclopropylcarbonyl chloride or 19 mg (0.15 mmol) of ethanesulfonyl chloride, and 1 mg of dimethylaminopyridine (DMAP) and the resulting mixture was stirred at 60° C. overnight. Since analysis by LC-MS revealed product formation, the reaction mixture was concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 17 mg (49% yield) of cyclopropanecarboxylic acid [6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-yl]-amide (415) as a yellow solid or 17 mg (46% yield) of ethanesulfonic acid [6-(4-benzyloxy-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidin-3-yl]-amide (421) as a yellow solid as indicated by LC-MS—calcd for C29H30N4O2 [M++H]+: 467.24, found: 467.2; calcd for C27H30N4O3S [M++H]+: 491.2, found: 491.2.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a residue which
  3. customwas purified via reverse-phase chromatography

Sources & evidence

ORD record
ord-ec159152a83646f09c0e8e66a7a9e1fc
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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