Hydrochloric Acid → HCID 68648282, compound

HRID 1162122Notes

Reaction equation

HRID 1162122 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][OH: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][CH2:15][OH: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 57470629HCID 57470629, compound

Product 1

HCID 68648282HCID 68648282, compoundYield 51%

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 (61 mg, 51%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.87 (s, 1H), 7.85 (d, J=9.8 Hz, 1H), 7.15 (,J=9.8 Hz, 1H), 6.93 (dt, J=7.0, 16.2 Hz, 1H), 6.66 (d, J=16.2 Hz, 1H), 3.62 (t, J=6.5 Hz, 2H), 3.43 (t, J=7.0 Hz, 2H), 2.37-2.32 (m, 2H), 1.82-1.76 (m, 2H), 1.69-1.64 (m, 2H), 1.56-1.50 (m, 2H), 1.47-1.41 (m, 2H), 0.96 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 157.1, 139.1, 133.3, 130.1, 120.9, 120.7, 117.7, 114.3, 62.6, 42.6, 34.2, 32.3, 31.2, 25.9, 23.3, 14.3; HPLC tR=11.2 min (Luna), 98.3%; ES-MS: (M+H)=289 m/z.

Sources & evidence

ORD record
ord-87ccf0e385f54a05a05c9a846103588d
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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