1-Hydroxybenzotriazole → HCID 70984149, compound

HRID 2283503Notes

Reaction equation

HRID 2283503 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][N:10]=2)[N:5]=[C:4]([C:19]2[CH:20]=[N:21][C:22]([C:25]3([OH:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:23][CH:24]=2)[CH:3]=1.[CH:32]1[CH:33]=[CH:34][C:35]2[N:40](O)N=[N:38][C:36]=2[CH:37]=1.[CH3:42]CN(C(C)C)C(C)C.N1C2C(=CC=C([C:61](O)=[O:62])C=2)C=CC=1>CN(C=O)C.C(Cl)CCl>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[C:13]([C:15]([F:17])([F:16])[F:18])[CH:12]=[CH:11][N:10]=2)[N:5]=[C:4]([C:19]2[CH:20]=[N:21][C:22]([C:25]3([OH:31])[CH2:30][CH2:29][N:28]([C:61]([C:35]4[N:40]=[C:42]5[NH:38][CH:36]=[CH:37][C:32]5=[CH:33][CH:34]=4)=[O:62])[CH2:27][CH2:26]3)=[CH:23][CH:24]=2)[CH:3]=1

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 599475Quinoline-7-carboxylic acidHCID 70984371HCID 70984371, compound

Product 1

HCID 70984149HCID 70984149, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a flask containing 4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)piperidin-4-ol (35 mg, 0.0.082 mmol), EDC (31 mg, 0.0.163 mmol), HOBt (25 mg, 0.163 mmol) and DIEA (0.071 mL, 0.408 mmol) in DMF (1.63 mL) was added 7-quinoline carboxylic acid (42 mg, 0.245 mmol). The solution was stirred at room temperature for 16 hours. The reaction solution was then filtered and purified by mass triggered reverse phase high pressure liquid chromatography to provide 4-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}-2,3′-bipyridin-6′-yl)-1-(1H-pyrrolo[2,3-b]pyridin-6-ylcarbonyl)piperidin-4-ol as a white solid. MS ESI calcd. for C30H26F3N7O2 [M+H]+ 574. found 574. 1H NMR (600 MHz, DMSO-d6) δ 11.79 (s, 1H), 10.22 (s, 1H), 9.15 (s, 1H), 8.53 (s, 1H), 8.48 (d, J=5.2 Hz, 1H), 8.45-8.37 (m, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.83-7.79 (m, 1H), 7.54 (s, 1H), 7.47 (s, 1H), 7.31 (s, 1H), 7.25 (d, J=8.0 Hz, 1H), 7.31-7.27 (m, 1H), 6.48 (s, 1H), 4.54-4.43 (m, 2H), 3.30-3.20 (m, 2H), 2.34 (s, 3H), 2.24-2.10 (m, 2H), 1.75-1.68 (m, 1H), 1.60-1.46 (m, 1H). rhSyk IC50=9 nM.

Workup

  1. filtrationThe reaction solution was then filtered
  2. custompurified by mass triggered reverse phase high pressure liquid chromatography

Sources & evidence

ORD record
ord-f4422e75332e4035a6a462cdb782db12
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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