Ethanol → HCID 18451062, compound

HRID 2390714Notes

Reaction equation

HRID 2390714 reaction equation
[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]/[CH2:34][CH2:35][N:36]2[C:44](=[O:45])[C:43]3C(=CC=CC=3)C2=O)=[CH:4][N:3]=1.NN.[CH2:49]([OH:51])[CH3:50]>>[C:44]([OH:45])(=[O:51])[CH3:43].[C:49]([OH:19])(=[O:51])[CH3:50].[C:44]([OH:45])(=[O:51])[CH3:43].[C:44]([OH:45])(=[O:51])[CH3:43].[NH2:1][C:2]1[C:7]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]4[N:21]([CH3:29])[C:22]5[C:27]([CH:28]=4)=[CH:26][CH:25]=[CH:24][CH:23]=5)=[O:19])=[C:13]([O:30][CH3:31])[CH:12]=3)=[CH:9][S:10][C:6]=2[C:5](/[CH:32]=[CH:33]/[CH2:34][CH2:35][NH2:36])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 18451059HCID 18451059, compound

Product 1

HCID 18451062HCID 18451062, compoundYield 1%

Procedure

A suspension of N-(4-{4-amino-7-[(1E)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)but-1-enyl]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.024 g, 0.038 mmol) in ethanol (5 mL) was treated with anhydrous hydrazine (0.01 g, 0.30 mmol). The reaction mixture was stirred at room temperature for 15 hours. The solvent was removed and the crude material was purified by preparative HPLC chromatography to give 0.001 g (1%) of the title compound as a tetraacetate salt. 1H NMR (DMSO-d6, 400 MHz) δ 9.55 (s, 1H), 8.05 (d, 1H), 8.03 (s, 1H), 7.70 (d, 1H), 7.60 (m, 2H), 7.35 (m, 2H), 7.20 (m, 1H), 7.15 (m, 1H), 7.10 (m, 1H), 6.60 (d, 1H), 6.30-6.20 (m, 1H), 5.60 (s, 3H), 4.05 (s, 3H), 3.95 (s, 3H), 2.75 (t, 2H), 2.40 (q, 2H); LCMS (conditions a) Rt 2.38 min (95%), M+ 498.3.

Workup

  1. customThe solvent was removed
  2. customthe crude material was purified by preparative HPLC chromatography

Sources & evidence

ORD record
ord-a6bab6abb9474cce962147c3fd1f508f
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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