3-(Cyclopropylaminocarbonyl)phenylboronic acid → HCID 16124310, compound

HRID 2060918Notes

Reaction equation

HRID 2060918 reaction equation
Cl[C:2]1[CH:10]=[C:9]([C:11]([NH:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:12])[C:8]([CH3:19])=[C:7]2[C:3]=1[C:4]1[CH:23]=[C:22]([CH3:24])[CH:21]=[N:20][C:5]=1[NH:6]2.[CH:25]1([NH:28][C:29]([C:31]2[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=2)=[O:30])[CH2:27][CH2:26]1>>[CH:25]1([NH:28][C:29]([C:31]2[CH:36]=[C:35]([C:2]3[CH:10]=[C:9]([C:11]([NH:13][CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])=[O:12])[C:8]([CH3:19])=[C:7]4[C:3]=3[C:4]3[CH:23]=[C:22]([CH3:24])[CH:21]=[N:20][C:5]=3[NH:6]4)[CH:34]=[CH:33][CH:32]=2)=[O:30])[CH2:26][CH2:27]1

Participants

3

Reactant 2

HCID 38742473-(Cyclopropylaminocarbonyl)phenylboronic acidHCID 16124309HCID 16124309, compound

Product 1

HCID 16124310HCID 16124310, compound

Procedure

The title compound was synthesized from 5-chloro-N-(2-(dimethylamino)ethyl)-3,8-dimethyl-9H-pyrido[2,3-b]indole-7-carboxamide and 3-(cyclopropylcarbamoyl)phenyl boronic acid using an analogous procedure to that described in the preparation of Compound 84. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.57 (dd, J=3.92, 2.40 Hz, 2H) 0.71 (dd, J=6.95, 2.40 Hz, 2H) 1.23 (s, 1H) 2.26 (s, 3H) 2.65 (s, 3H) 2.87 (d, J=5.05 Hz, 6H) 3.29 (q, J=5.98 Hz, 2H) 3.61 (q, J=6.15 Hz, 2H) 7.20 (s, 1H) 7.50 (s, 1H) 7.66 (t, J=7.83 Hz, 1H) 7.77 (d, J=7.83 Hz, 1H) 7.98 (d, J=7.83 Hz, 1H) 8.08 (s, 1H) 8.31 (d, J=1.77 Hz, 1H) 8.57-8.61 (m, 1H) 8.59 (d, J=4.55 Hz, 1H) 12.05 (s, 1H). [M+H] calc'd for C28H31N5O2 470; found, 470.4.

Sources & evidence

ORD record
ord-1eefcb619d2d49eb848d5ddf56acfc06
Source dataset
uspto-grants-2012_10
Patent number
US08278450B2

Reaction notes

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