HCID 70654985, compound → HCID 70654527, compound

HRID 2091592Notes

Reaction equation

HRID 2091592 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:20]=[CH:19][C:12]3[C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH2:17][C:11]=3[CH:10]=2)O1.[NH2:22][C:23]1[N:24]=[CH:25][C:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([N:39]([CH2:41][CH3:42])[CH3:40])(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[N:27][C:28]=1Br>>[NH2:22][C:23]1[N:24]=[CH:25][C:26]([C:30]2[CH:35]=[CH:34][C:33]([S:36]([N:39]([CH2:41][CH3:42])[CH3:40])(=[O:37])=[O:38])=[CH:32][CH:31]=2)=[N:27][C:28]=1[C:9]1[CH:20]=[CH:19][C:12]2[C:13](=[O:18])[NH:14][CH2:15][CH2:16][CH2:17][C:11]=2[CH:10]=1

Participants

3

Reactant 2

HCID 70654985HCID 70654985, compoundHCID 86670216HCID 86670216, compound

Product 1

HCID 70654527HCID 70654527, compoundYield 25.2%

Procedure

General method C was applied to 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one (95 mg, 0.33 mmol) and 4-(5-amino-6-bromopyrazin-2-yl)-N-ethyl-N-methylbenzenesulfonamide (108 mg, 0.29 mmol) to provide 4-(5-amino-6-(1-oxo-2,3,4,5-tetrahydro-1H-benzo[c]azepin-7-yl)pyrazin-2-yl)-N-ethyl-N-methylbenzenesulfonamide (33 mg, 22% yield) after purification by preparatory HPLC. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.70 (s, 1H), 8.22 (d, J=8.5 Hz, 2H), 8.12 (t, J=5.8 Hz, 1H), 7.80 (d, J=8.5 Hz, 2H), 7.71 (dd, J=8.0, 1.5 Hz, 1H), 7.62-7.66 (m, 2H), 6.66 (br. s, 2 H), 2.93-3.09 (m, 4H), 2.83 (t, J=1.0 Hz, 2H), 2.67 (s, 3H), 1.94 (dd, J=12.3, 6.0 Hz, 2H), 1.03 (t, J=7.2 Hz, 3H); MS (EI) m/z=452.5 [M+1]+.

Sources & evidence

ORD record
ord-783e85bdfdce4cd8a531a80b2777baca
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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