Ammonia → 2-[2-(Difluoromethyl)-4-methoxy-1h-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9h-purine

HRID 516416노트

반응식

HRID 516416 반응식
[F:1][CH:2]([F:42])[C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)=[C:10]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:9]=2)[C:6]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:5]=2[N:4]=1.C(O)(C(F)(F)F)=O.N>C(Cl)Cl>[F:42][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[CH:13][N:14]3[CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[C:10]([N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[N:9]=2)[C:6]2[CH:36]=[CH:37][CH:38]=[C:39]([O:40][CH3:41])[C:5]=2[N:4]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 67543947tert-butyl 4-[2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-9H-purin-9-yl]-1-piperidinecarboxylate

생성물 1

HCID 666981762-[2-(Difluoromethyl)-4-methoxy-1h-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9h-purine수율 88.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Reaction of the above carbamate (165 mg, 0.282 mmol) with an excess of TFA (2 mL) in CH2Cl2 (10 mL) at room temperature for 1.5 hrs, followed by treatment with aq. NH3 gave 2-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-9-(4-piperidinyl)-9H-purine (121 mg, 88%), which was used in the next step without further purification: 1H NMR (CDCl3) δ 7.87 (s, 1H), 7.81 (dd, J=8.4, 0.5 Hz, 1H), 7.48 (t, J=53.6 Hz, 1H), 7.35 (t, J=8.2 Hz, 1H), 6.81 (d, J=7.8 Hz, 1H), 4.54 (tt, J=12.0, 4.1 Hz, 1H), 4.38 (br s, 4H), 4.07 (s, 3H), 3.88 (t, J=4.8 Hz, 4H), 3.30 (d, J=12.4 Hz, 2H), 2.86 (dt, J=12.4, 2.3 Hz, 2H), 2.20 (dd, J=11.8, 2.2 Hz, 2H), 2.04 (dq, J=12.3, 4.1 Hz, 2H).

출처 및 근거

ORD 기록
ord-4cac52ff6748414abf45f29aaca82944
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108980B2

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