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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 223063
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HRID 223063 반응식
[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]
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참가 물질

5

반응물 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

생성물 1

HCID 86608573
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
수율 40%

실험 절차

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)+.

후처리

  1. customSeparation by HPLC with TFA

출처 및 근거

ORD 기록
ord-17952c55f027499fb101d4bd07923574
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08207176B2

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