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Diisopropylethylamine → N-(3-(methylsulfonamido)phenyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide

HRID 593718
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HRID 593718 반응식
[C:1]1([C:7]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:8]=2[C:9]([NH:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)=[N:10][N:11]=[C:12]3[C:17]2[CH:18]=[N:19][CH:20]=[C:21]([CH:25]=2)[C:22]([OH:24])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:34][C:35]1[CH:36]=[C:37]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])[CH:38]=[CH:39][CH:40]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:45][S:42]([NH:41][C:37]1[CH:36]=[C:35]([NH:34][C:22](=[O:24])[C:21]2[CH:25]=[C:17]([C:12]3[C:13]4[C:8](=[C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)[CH:16]=[CH:15][CH:14]=4)[C:9]([NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[N:10][N:11]=3)[CH:18]=[N:19][CH:20]=2)[CH:40]=[CH:39][CH:38]=1)(=[O:44])=[O:43]
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참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 2734262N-(3-Aminophenyl)methanesulfamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 904238795-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinic acid

생성물 1

HCID 86267256
N-(3-(methylsulfonamido)phenyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide
수율 27.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-(5-Phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinic acid (15.0 mg, 0.0350 mmol) was added to N-(3-aminophenyl)methanesulfonamide (7.73 mg, 0.0420 mmol) and a solution of HATU (19.7 mg, 0.0520 mmol) and DIPEA (0.0180 mL, 0.104 mmol) in DMF (0.5 mL) was added. The reaction mixture was stirred for 5 hours at room temperature. The volatile components were removed under high vacuum and the residue was purified by reverse phase preparative HPLC (Condition 36 as described in general methods) to afford N-(3-(methylsulfonamido)phenyl)-5-(5-phenyl-4-((pyridin-2-ylmethyl)amino)phthalazin-1-yl)nicotinamide (5.79 mg, 26.4%) as a white solid. LCMS (Condition 37): retention time 1.63 min, [M+1]=602.1, purity 95.02%. 1H NMR (400 MHz, DMSO-d6) δ 3.01 (s, 3 H), 4.67 (d, J=4.4 Hz, 2 H), 6.34 (t, J=4.4 Hz, 1 H), 6.95-6.99 (m, 1 H), 7.21-7.24 (m, 1 H), 7.28 (d, J=8.0 Hz, 1 H), 7.30 (t, J=8.0 Hz, 1 H), 7.50-7.58 (m, 6 H), 7.68-7.77 (m, 3 H), 7.90-7.94 (m, 2 H), 8.22-8.24 (m, 1 H), 8.61 (t, J=2.0 Hz, 1 H), 9.05 (d, J=2.0 Hz, 1 H), 9.26 (d, J=2.0 Hz, 1 H), 10.60 (s, 1 H).

후처리

  1. customThe volatile components were removed under high vacuum
  2. customthe residue was purified by reverse phase preparative HPLC (Condition 36 as described in general methods)

출처 및 근거

ORD 기록
ord-56f2c5342c734338a630fd683ecd1479
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242966B2

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