Hydrochloric Acid → HCID 68647934, compound

HRID 1162130Notes

Reaction equation

HRID 1162130 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:17](/B(O)O)=[CH:18]\[CH2:19][CH2:20][CH2:21][CH3:22].[ClH:26]>CCOCC>[ClH:26].[CH:17](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:18]\[CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 57470630HCID 57470630, compound

Product 1

HCID 68647934HCID 68647934, compoundYield 54%

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 (43 mg, 54%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.53 (d, J=9.7 Hz, 1H), 7.42 (s, 1H), 6.78 (dt, J=16.1, 7.0 Hz, 1H), 6.64-6.58 (m, 2H), 3.53 (t, J=6.2 Hz, 2H), 3.44 (t, J=6.2 Hz, 2H), 3.35 (s, 3H), 2.30-2.26 (m, 2H), 1.97-1.92 (m, 2H), 1.53-1.40 (m, 4H), 0.96 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 157.1, 139.2, 133.2, 130.0, 121.0, 120.6, 117.8, 114.3, 71.4, 59.0, 40.0, 34.3, 32.3, 29.4, 23.3, 14.3; HPLC tR=12.3 min, 98.6%; ES-MS: (M+H)=289 m/z.

Sources & evidence

ORD record
ord-fc6dc20fc25242c489d7a50348af6648
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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