Dichloromethane → 3-[2-{[3-(Diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-5-fluoro-4-methylbenzoic acid trifluoroacetate

HRID 2245157Notes

Reaction equation

HRID 2245157 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([N:10]([CH2:49][CH3:50])[CH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:16]=[C:17]([C:34]2[CH:35]=[C:36]([CH:44]=[C:45]([F:48])[C:46]=2[CH3:47])[C:37]([O:39]C(C)(C)C)=[O:38])[C:18]2[CH:24]=[CH:23][C:22](=[O:25])[N:21]([C:26]3[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=3[F:33])[C:19]=2[N:20]=1)[CH3:9].ClCCl.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:49]([N:10]([CH2:8][CH3:9])[CH2:11][CH2:12][CH2:13][NH:14][C:15]1[N:16]=[C:17]([C:34]2[CH:35]=[C:36]([CH:44]=[C:45]([F:48])[C:46]=2[CH3:47])[C:37]([OH:39])=[O:38])[C:18]2[CH:24]=[CH:23][C:22](=[O:25])[N:21]([C:26]3[C:27]([F:33])=[CH:28][CH:29]=[CH:30][C:31]=3[F:32])[C:19]=2[N:20]=1)[CH3:50]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 866085741,1-Dimethylethyl 3-[2-{[3-(diethylamino)-propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-5-fluoro-4-methylbenzoate trifluoroacetate

Product 1

HCID 866085733-[2-{[3-(Diethylamino)propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-5-fluoro-4-methylbenzoic acid trifluoroacetateYield 40%

Procedure

To the crude compound 1,1-dimethylethyl 3-[2-{[3-(diethylamino)-propyl]amino}-8-(2,6-difluorophenyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-5-fluoro-4-methylbenzoate trifluoroacetate in dichloromethane (1.5 mL, 23.3 mmol) were added TFA (0.703 mL, 9.5 mmol) and triethylsilane (0.281 mL, 1.82 mmol). The mixture was stirred at rt overnight. Separation by HPLC with TFA afforded the title compound (301 mg, 40%, 2 steps yield). LC-MS m/z 540 (M+H)+.

Workup

  1. customSeparation by HPLC with TFA

Sources & evidence

ORD record
ord-d2ce527c738842bba35748354b6b1cc0
Source dataset
uspto-grants-2010_03
Patent number
US07678801B2

Reaction notes

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