Hydrochloric Acid → HCID 68648514, compound

HRID 1162124Notes

Reaction equation

HRID 1162124 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:22](/B(O)O)=[CH:23]\[CH2:24][CH2:25][CH2:26][CH3:27].[ClH:31]>CCOCC>[ClH:31].[CH:22](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:23]\[CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 68647897HCID 68647897, compound

Product 1

HCID 68648514HCID 68648514, compoundYield 35%

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 (60 mg, 35%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.59 (d, J=9.7 Hz, 1H), 7.50 (s, 1H), 6.77-6.69 (m, 2H), 6.61 (d, J=16.2 Hz, 1H), 3.45 (t, J=6.7 Hz, 2H), 3.35 (m, 2H), 3.13-2.69 (m, 11H), 2.29 (q, J=6.7 Hz, 2H), 2.02-1.93 (m, 2H), 1.53-1.38 (m, 4H), 0.96 (t, J=7.1 Hz, 13C NMR (125 MHz, CD3OD) δ 155.6, 137.1, 133.8, 128.9, 127.2, 125.0, 116.5, 114.6, 56.3, 54.5, 51.8, 44.1, 40.4, 34.4, 32.9, 26.2, 23.4, 14.4; HPLC tR=8.7 min (Luna), 95.1%; ES-MS: (M+H)=357 m/z.

Sources & evidence

ORD record
ord-64dbcb35c3db4ab5b3f1ac1058e710e8
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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