Diisopropylethylamine → 4-[4-(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-3-methoxy-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1262117

반응식

HRID 1262117 반응식
[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8](O)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([C:49]2[CH:54]=[CH:53][C:52]([NH2:55])=[C:51]([O:56][CH3:57])[CH:50]=2)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.[Cl-].[Na+].O.O>[C:36]([O:40][C:41]([N:43]1[CH2:44][CH2:45][CH:46]([C:49]2[CH:54]=[CH:53][C:52]([NH:55][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([Br:1])[N:10]4[N:9]=3)=[C:51]([O:56][CH3:57])[CH:50]=2)[CH2:47][CH2:48]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]

참가 물질

8

반응물 4

HCID 81531DiisopropylethylamineHCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylateHCID 178517419HCID 178517419, 화합물

생성물 1

HCID 667116754-[4-(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-3-methoxy-phenyl]-piperidine-1-carboxylic acid tert-butyl ester수율 52%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

In a 10 mL sealed tube, to 7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ol (150.0 mg, 0.701 mmol) and N,N-Diisopropylethylamine (0.488 mL, 2.80 mmol) in 3.8 mL of anhydrous DMF was added N-Phenylbis(trifluoromethanesulfonimide (263 mg, 0.736 mmol). After stirring at room temperature for 2 hours, 4-(4-Amino-3-methoxy-phenyl)-piperidin-1-carboxylic acid tert-butyl ester (214.7 mg, 0.701 mmol) was added. The reaction mixture was heated at 65° C. for 4 hours. The reaction was conc. in vacuo. Water and brine were added and the contents were extracted with DCM. The combined organic layers were dried with sodium sulfate, filtered, and conc. in vacuo. The reaction mixture was purified via silica gel column chromatography using 100:1 DCM:MeOH as the eluant to afford a the title compound as a red oil (52%). 1H NMR (DMSO-d6)-8.89 (s, 1H), 8.23 (d, 1H, J=8.20 Hz), 7.83 (s, 1H), 6.98-6.95 (m, 2H), 6.91 (d, 1H, J=4.72 Hz), 6.85 (d, 1H, J=8.52 Hz), 4.66-4.55 (br s, 1H), 4.16-3.99 (m, 3H), 3.89 (s, 3H), 2.87-2.75 (m, 2H), 1.78 (d, 2H, J=12.93 Hz), 1.70 (d, 1H, J=12.57 Hz), 1.42 (s, 9H).

후처리

  1. customIn a 10 mL sealed tube
  2. temperatureThe reaction mixture was heated at 65° C. for 4 hours
  3. extractionthe contents were extracted with DCM
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. customThe reaction mixture was purified via silica gel column chromatography

출처 및 근거

ORD 기록
ord-c1ca8e1bc4c4455ebde5b81242c927a4
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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