Formaldehyde → Trifluoroacetic acid

HRID 2067897노트

반응식

HRID 2067897 반응식
[F:1][CH:2]([F:37])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24]([N:26]4[CH2:31][CH2:30][NH:29][CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])[CH:22]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.[CH2:38]=[O:39].[O-:40]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[F:37][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH3:36])=[C:21]([NH:23][C:24]([N:26]4[CH2:31][CH2:30][N:29]([CH3:38])[CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])[CH:22]=3)=[N:14][CH:15]=2)=[CH:8][CH:9]=1.[C:38]([OH:40])([C:32]([F:35])([F:34])[F:33])=[O:39]

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 24436Sodium SulfateHCID 58542195N-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)piperazine-1-carboxamide

생성물 2

HCID 6422Trifluoroacetic acidHCID 25196951N-(5-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)-4-methylpiperazine-1-carboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N-(5-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)piperazine-1-carboxamide D11 (0.05 mmol), HCHO (0.15 mmol, 30% aqueous) and anhydrous Na2SO4 (1.5 mmol) in DCM (2 mL) is stirred at rt for 30 min. Then NaHB(OAc)3 (0.3 mmol) is added and the resulting mixture is stirred for 12 h. Purification by prep-HPLC (ACN gradient 10-70%) affords N-(5-(5-(4-(Difluoromethoxy)phenyl)pyrimidin-2-ylamino)-2-methylphenyl)-3-(trifluoromethyl)-4-methylpiperazine-1-carboxamide D12 as a TFA salt. 1H NMR (400 MHz, d6-DMSO) δ 9.69 (s, 1H), 8.80 (s, 2H), 8.15 (s, 1H), 7.76 (d, J=8.8 Hz, 2H), 7.61 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 7.28 (t, J=74.0 Hz, 1H), 7.27 (d, J=8.8 Hz, 2H), 7.09 (d, J=8.4 Hz, 1H), 3.68 (m, 1H), 3.54 (m, 1H), 2.88 (m, 1H), 2.51 (m, 4H), 2.47 (s, 1H), 2.09 (s, 3H). MS (m/z) (M+1)+: 537.2.

후처리

  1. customPurification by prep-HPLC (ACN gradient 10-70%)

출처 및 근거

ORD 기록
ord-fc40094233ae45858407ed95ec5028a5
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293757B2

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