Hydrochloric Acid → HCID 68647711, compound

HRID 1162132Notes

Reaction equation

HRID 1162132 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][OH:14])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:15](/B(O)O)=[CH:16]\[CH2:17][CH2:18][CH2:19][CH3:20].[ClH:24]>CCOCC>[ClH:24].[CH:15](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][OH:14])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:16]\[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 57418689HCID 57418689, compound

Product 1

HCID 68647711HCID 68647711, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2. The free-base was converted to the HCl salt with 2N HCl in Et2O to provide the title compound (45 mg, 53%) as a white solid; 1H NMR (500 MHz, CD3OD) δ 7.91 (s, 1H), 7.88 (d, J=9.8 Hz, 1H), 7.22 (d, J=9.8 Hz, 1H), 6.88 (dt, J=7.0, 16.2 Hz, 1H), 6.67 (d, J=16.2 Hz, 1H), 3.81 (t, J=5.7 Hz, 2H), 3.55 (t, J=5.7 Hz, 2H), 2.36-2.32 (m, 2H), 1.55-1.49 (m, 2H), 1.46-1.40 (m, 2H), 0.96 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 157.3, 139.2, 133.2, 130.2, 121.0, 120.8, 117.6, 114.2, 60.5, 45.0, 34.3, 32.3, 23.3, 14.3; HPLC tR=10.8 min (Luna), 98.8%; ES-MS: (M+H)=261 m/z.

Sources & evidence

ORD record
ord-1504634363e0424781a64abdd94bcc86
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

Loading…