Ethanol → N-(4-{4-amino-7-[3-(4-hydroxypiperidin-1-yl)propyl]thieno[3,2-c]pyridin-3-yl}2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

HRID 17248Notes

Reaction equation

HRID 17248 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][N:35]2[CH2:40][CH2:39][CH:38]([OH:41])[CH2:37][CH2:36]2)=[CH:4][N:3]=1.C(O)C.OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O.[H][H]>[OH-].[OH-].[Pd+2].C(O)(=O)C>[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]([CH2:32][CH2:33][CH2:34][N:35]2[CH2:36][CH2:37][CH:38]([OH:41])[CH2:39][CH2:40]2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 441036D-PsicoseHCID 11238420N-(4-(4-amino-7-(3-(4-hydroxypiperidin-1-yl)prop-1-enyl)thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 18451118N-(4-{4-amino-7-[3-(4-hydroxypiperidin-1-yl)propyl]thieno[3,2-c]pyridin-3-yl}2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamideYield 26.7%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

N-(4-{4-Amino-7-[(1E)-3-(4-hydroxypiperidin-1-yl)prop-1-enyl]thieno [3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (130 mg, 0.23 mmol), ethanol (25 mL), and acetic acid (0.65 mL) were combined in a hydrogenation vessel, purged, and palladium hydroxide on carbon (45 mg, 50% weight dispersion in oil, 0. 16 mmol) was added. 50 Psi of hydrogen was applied for 16 hours. The mixture was filtered and purified by RP-HPLC to yield the title compound (35 mg, 25% yield) after lyophilization: 1H NMR (DMSO, 400 MHz) δ 9.50 (s, 1H), 7.98 (d, 1H), 7.70-7.72 (m, 2H), 5.59 (d, 1H), 7.54 (s, 1H), 7.07-7.35 (m, 3H), 5.34 (bs, 2H), 4.58 (bs, 1H), 4.04 (s, 3H), 3.91 (s, 3H), 2.71 (t, 2H), 2.28 (t, 2H), 1.97 (t, 2H), 1.90 (s, 3H), 1.82 (t, 2H), 1.70 (m, 1H), 1.40 (q, 2H); RP-HPLC (Conditions i) Rt 10.0 min. MS: 568.3 MH−.

Workup

  1. custompurged
  2. filtrationThe mixture was filtered
  3. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-1fc28454c7134c3791324a2e202c5bf4
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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