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Acetic Acid → 4-(4-Methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3'-bipyridin-6'-ylamino)piperidine-1-carboxamide

HRID 2283501
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HRID 2283501 반응식
[O-:1][C:2]#[N:3].[K+].C(O)(=O)C.[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][N:18]=2)[N:13]=[C:12]([C:27]2[CH:28]=[N:29][C:30]([NH:33][CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)=[CH:31][CH:32]=2)[CH:11]=1>C1COCC1>[CH3:9][C:10]1[CH:15]=[C:14]([NH:16][C:17]2[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][N:18]=2)[N:13]=[C:12]([C:27]2[CH:28]=[N:29][C:30]([NH:33][CH:34]3[CH2:39][CH2:38][N:37]([C:2]([NH2:3])=[O:1])[CH2:36][CH2:35]3)=[CH:31][CH:32]=2)[CH:11]=1
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참가 물질

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반응물 3

HCID 176Acetic AcidHCID 11378442Potassium cyanateHCID 867320004-Methyl-N6'-(piperidin-4-yl)-N6-(4-(trifluoromethyl)pyridin-2-yl)-2,3'-bipyridine-6,6'-diamine

생성물 1

HCID 709837074-(4-Methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3'-bipyridin-6'-ylamino)piperidine-1-carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Potassium cyanate (9.47 mg, 0.117 mmol), acetic acid (0.017 mL, 0.292 mmol), 4-methyl-N6′-(piperidin-4-yl)-N6-(4-(trifluoromethyl)pyridin-2-yl)-2,3′-bipyridine-6,6′-diamine (25 mg, 0.058 mmol), and THF (1 mL) were combined. The mixture was stirred at room temperature for 16 hours. The crude solution was purified via reverse phase high pressure liquid chromatography to afford 4-(4-methyl-6-(4-(trifluoromethyl)pyridin-2-ylamino)-2,3′-bipyridin-6′-ylamino)piperidine-1-carboxamide. MS ESI calcd. for C23H25F3N7O [M+H]+ 472. found 472. 1H NMR (500 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.53-8.49 (m, 3H), 8.28 (s, 1H), 8.24 (d, J=6.5 Hz, 1H), 7.44 (s, 1H), 7.39 (s, 1H), 7.22-7.16 (m, 2H), 4.42 (m, 1H), 3.80 (m, 1H), 3.72-3.65 (m, 2H), 3.45 (dd, J=11.0, 4.0 Hz, 1H), 2.36 (s, 3H), 2.22 (m, 1H), 2.00 (m, 1H), 1.82 (s, 3H). rhSyk IC50=4 nM.

후처리

  1. customThe crude solution was purified via reverse phase high pressure liquid chromatography

출처 및 근거

ORD 기록
ord-4bebbe1a4250412e99b2d3a2ee72be3d
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09145391B2

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