Ethanolamine → 3-[4-(4-Methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid (2-hydroxy-ethyl)amide

HRID 1506009ノート

反応式

HRID 1506009 の反応式
[CH3:1][CH2:2][N:3]([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])C.CN1CCN(C2C=[CH:21][C:20]([C:23]3[CH:38]=[N:37][C:26]4[NH:27][C:28]5[CH:33]=[N:32][C:31]([C:34]([OH:36])=O)=[CH:30][C:29]=5[C:25]=4[CH:24]=3)=[CH:19]C=2)CC1.C1C[N:42]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:41]C1.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[CH2:82]([CH2:84][NH2:85])[OH:83].S(=O)(=O)(O)O>CN(C=O)C>[OH:83][CH2:82][CH2:84][NH:85][C:34]([C:31]1[N:32]=[CH:33][C:28]2[NH:27][C:26]3[N:37]=[CH:38][C:23]([C:20]4[CH:19]=[CH:9][C:7]([N:3]5[CH2:2][CH2:1][N:42]([CH3:41])[CH2:6][CH2:4]5)=[CH:8][CH:21]=4)=[CH:24][C:25]=3[C:29]=2[CH:30]=1)=[O:36]

参加物

8

反応物 6

HCID 700EthanolamineHCID 1118Sulfuric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 582665593-[4-(4-Methylpiperazin-1-Yl)phenyl]-9h-Pyrrolo[2,3-B:5,4-C']dipyridine-6-Carboxylic Acid

生成物 1

HCID 582664473-[4-(4-Methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carboxylic acid (2-hydroxy-ethyl)amide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (13.5 μL, 77.4 μmol) was added to a solution of 3-[4-(4-methylpiperazin-1-yl)-phenyl]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carboxylic acid (20.0 mg, 51.6 PyBOP (28.2 mg, 54.2 μmol) and HOBt (8.4 mg, 62 μmol) in DMF (0.6 mL). After 10 min at ambient temperature, ethanolamine (16 μL, 0.26 mmol) was added to the reaction mixture. After 30 min the resultant mixture was acidified with 10% aqueous sulfuric acid and concentrated in vacuo. The resultant residue was dissolved in DMF, water and 10% aqueous sulfuric acid and purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min) to afford the title compound. 1H NMR (DMSO-D6, 400 MHz): 12.49 (s, 1H), 9.71 (br.s, 1H), 9.14 (d, J=2.1 Hz, 1H), 8.90 (s, 1H), 8.94 (d, J=2.2 Hz, 1H), 8.66 (t, J=5.8 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.17 (d, J=8.8 Hz, 2H), 3.97 (d, J=13.4 Hz, 2H), 3.57 (m, 4H), 3.45 (m, 2H), 3.20 (m, 2H), 3.04 (m, 2H), 2.89 (s. 3H), LCMS (Method D): RT=6.31 min, M+H+=431.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in DMF
  3. customwater and 10% aqueous sulfuric acid and purified by preparative HPLC (0-30% MeCN over 30 min, 35 mL/min)

出典と根拠

ORDレコード
ord-d133a40a56394957b9af359348dde362
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

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