Trifluoroacetic acid → HCID 22258789, compound

HRID 1611209Notes

Reaction equation

HRID 1611209 reaction equation
[NH2:1]/[CH:2]=[N:3]/[C:4]1[C:9]([C:10]#[N:11])=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)[CH:7]=[C:6]([C:25]2[C:30]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)=[CH:29][CH:28]=[CH:27][C:26]=2[O:41][CH2:42][CH:43]2[CH2:45][CH2:44]2)[N:5]=1.FC(F)(F)C(O)=O>CO.C1(C)C=CC=CC=1>[NH2:11][C:10]1[C:9]2[C:8]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]3)=[CH:7][C:6]([C:25]3[C:30]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=4)=[CH:29][CH:28]=[CH:27][C:26]=3[O:41][CH2:42][CH:43]3[CH2:44][CH2:45]3)=[N:5][C:4]=2[N:3]=[CH:2][N:1]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22258723HCID 22258723, compound

Product 1

HCID 22258789HCID 22258789, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl 3-(2-{[(1E)-aminomethylidene]amino}-3-cyano-6-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]phenyl}-4-pyridinyl)-1-piperidinecarboxylate (0.180 g, 0.289 mmol) in MeOH (5 mL) and toluene (5 mL) was added trifluoroacetic acid (0.01 mL). The mixture was allowed to stand for 20 days and concentrated under reduced pressure. Purification by column chromatography on silica gel (CH2Cl2/MeOH 50:1 to 20:1) gave tert-butyl 3-(4-amino-7-{2-(cyclopropylmethoxy)-6-[(4-methoxybenzyl)oxy]-phenyl}pyrido[2,3-d]pyrimidin-5-yl)-1-piperidinecarboxylate as a colorless oil (0.026 g, yield; 15%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification by column chromatography on silica gel (CH2Cl2/MeOH 50:1 to 20:1)

Sources & evidence

ORD record
ord-464b90b4e82542169e5fd1a909d8fafd
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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