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

HRID 593718
ノート
印刷プレビュー

反応式

HRID 593718 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-56f2c5342c734338a630fd683ecd1479
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242966B2

反応ノート

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