HCID 70654978, compound → HCID 70654389, compound

HRID 2091581Notes

Reaction equation

HRID 2091581 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][C:7]=1Br.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[CH:33][C:34]3[C:40](=[O:41])[NH:39][CH2:38][CH2:37][NH:36][C:35]=3[CH:42]=2)O1>>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[N:6][C:7]=1[C:31]1[CH:32]=[CH:33][C:34]2[C:40](=[O:41])[NH:39][CH2:38][CH2:37][NH:36][C:35]=2[CH:42]=1

Participants

3

Reactant 2

HCID 70654978HCID 70654978, compoundHCID 86670211HCID 86670211, compound

Product 1

HCID 70654389HCID 70654389, compoundYield 33%

Procedure

General method C was applied to 4-(4-(5-amino-6-bromopyrazin-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile (215 mg, 0.6 mmol) and 8-(4,4,5,5-tetra methyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (173 mg, 0.6 mmol) to provide 4-(4-(5-amino-6-(5-oxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-8-yl)pyrazin-2-yl)phenyl)tetrahydro-2H-pyran-4-carbonitrile as a yellow solid (87 mg, 33% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.47 (s, 1H), 8.14 (d, J=8.3 Hz, 1H), 8.01 (d, J=8.3 Hz, 2 H), 7.58 (d, J=8.3 Hz, 2H), 7.21 (d, J=8.3 Hz, 1H), 7.04 (s, 1H), 6.40 (br. s., 1H), 4.93 (br. s., 2H), 4.57 (br. s., 1H), 4.12 (d, J=8.8 Hz, 2H), 3.94 (t, J=11.7 Hz, 2H), 3.50-3.73 (m, 4 H), 2.02-2.26 (m, 4H); MS (EI) m/z=441.5 [M+1]+.

Sources & evidence

ORD record
ord-69904b532e424b72a1e96887ec53912a
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

Loading…