Diisopropylethylamine → Ammonia methanol

HRID 1262116노트

반응식

HRID 1262116 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15](O)=[N:16]2)=[CH:11][CH:10]=1.C(N(CC)C(C)C)(C)C.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([N:41]2[CH:45]=[C:44]([NH2:46])[CH:43]=[N:42]2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C>[NH3:14].[CH3:1][OH:2].[C:28]([O:32][C:33]([N:35]1[CH2:36][CH2:37][CH:38]([N:41]2[CH:45]=[C:44]([NH:46][C:15]3[N:14]=[CH:13][C:12]4=[CH:11][CH:10]=[C:9]([C:4]5[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=5[O:2][CH3:1])[N:17]4[N:16]=3)[CH:43]=[N:42]2)[CH2:39][CH2:40]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 27281520tert-butyl 4-(4-amino-1H-pyrazol-1-yl)piperidine-1-carboxylateHCID 1784892767-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol

생성물 2

HCID 21705897Ammonia methanolHCID 667111544-{4-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In a 10 mL sealed tube, to 7-(2-Methoxyphenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (90.58 mg, 0.376 mmol) and N,N-Diisopropylethylamine (0.262 mL, 1.50 mmol) in 2.0 mL of anhydrous DMF was added N-Phenylbis(trifluoromethane)sulfonamide) (211.1 mg, 0.591 mmol). After stirring at room temperature for 2 hours, 4-(4-Amino-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.376 mmol) (synthesized according to literature procedure, Tet. Lett. 2008, 49, 2996) was added. The reaction mixture was heated at 65° C. overnight. The reaction was conc. in vacuo. The reaction mixture was purified via silica gel column chromatography using 100:1 DCM:MeOH then 500:15:10 DCM:MeOH:7N NH3/MeOH to afford the title compound as an orange foam. MP 95-100° C. LCMS (E/I+) 490.19 (M+H). 1H NMR (DMSO-d6)-9.32 (s, 1H), 8.88 (s, 1H), 7.72 (d, 1H, J=7.32 Hz), 7.69 (s, 1H), 7.48 (t, 1H, J=7.78 Hz), 7.36 (s, 1H), 7.20 (d, 1H, J=8.32 Hz), 7.11 (t, 1H, J=7.44 Hz), 6.88 (d, 1H, J=4.60 Hz), 6.85 (d, 1H, J=4.60 Hz), 4.22-4.11 (m, 1H), 4.11-3.98 (m, 2H), 3.76 (s, 3H), 3.00-2.76 (m, 2H), 1.93-1.84 (m, 2H), 1.58-1.49 (m, 2H), 1.47 (9H).

후처리

  1. customIn a 10 mL sealed tube
  2. temperatureThe reaction mixture was heated at 65° C. overnight
  3. customThe reaction mixture was purified via silica gel column chromatography

출처 및 근거

ORD 기록
ord-f9b6632a4fe043af855f83b6650990f1
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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