Trifluoroacetic acid → 1-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid[1-methyl-6-(2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-5-yloxy)-1H-indazol-3-yl]-amide

HRID 1045507

Reaction equation

HRID 1045507 reaction equation
COC1C=CC(C[N:8]2[CH2:13][C:12]3[C:14]([O:18][C:19]4[CH:27]=[C:26]5[C:22]([C:23]([NH:29][C:30]([C:32]6[C:33](=[O:45])[N:34]([C:38]7[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=7)[CH:35]=[CH:36][CH:37]=6)=[O:31])=[N:24][N:25]5[CH3:28])=[CH:21][CH:20]=4)=[CH:15][CH:16]=[N:17][C:11]=3[NH:10][C:9]2=[O:46])=CC=1.FC(F)(F)C(O)=O>>[CH3:28][N:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([O:18][C:14]3[C:12]4[CH2:13][NH:8][C:9](=[O:46])[NH:10][C:11]=4[N:17]=[CH:16][CH:15]=3)[CH:27]=2)[C:23]([NH:29][C:30]([C:32]2[C:33](=[O:45])[N:34]([C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[CH:35]=[CH:36][CH:37]=2)=[O:31])=[N:24]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 704970111-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylicacid{6-[3-(4-methoxy-benzyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-5-yloxy]-1-methyl-1H-indazol-3-yl}-amide

Product 1

HCID 704982091-(4-Fluoro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid[1-methyl-6-(2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-5-yloxy)-1H-indazol-3-yl]-amideYield 82.5%

Conditions

Temperature
80 °C

Procedure

A solution of compound 278 (22.00 mg; 0.03 mmol; 1.00 eq.) and trifluoroacetic acid (2.00 ml) was stirred at 80 degrees C. overnight. The reaction was stirred at 80 degrees C. for 22 hr. The reaction was concentrated, redissolved in DMSO, and treated with Et3N to pH 8. The solution was then purified directly via prep HPLC to afford 13 mg (60%) of 279 as a yellow solid. LC-MS (M+H=526, obsd.=526).

Workup

  1. customovernight
  2. concentrationThe reaction was concentrated
  3. dissolutionredissolved in DMSO
  4. additiontreated with Et3N to pH 8
  5. customThe solution was then purified directly via prep HPLC

Sources & evidence

ORD record
ord-e29d7cace7f14278a10abbbf4ee75ec7
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Linked notes

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