Hydrochloric Acid → HCID 68648779, compound

HRID 1162142Notes

Reaction equation

HRID 1162142 reaction equation
Br[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:20](/B(O)O)=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:41].Cl.Cl>CCOCC>[ClH:41].[ClH:41].[CH:20](/[C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:21]\[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 5326225B-(1E)-1-Hexenylboronic acidHCID 58857922HCID 58857922, compound

Product 1

HCID 68648779HCID 68648779, compoundYield 36%

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 dihydrochloride salt with 2N HCl in Et2O to provide the title compound (59 mg, 36%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.97 (s, 1H), 7.92 (d, J=9.9 Hz, 1H), 7.23 (d, J=9.9 Hz, 1H), 6.87-6.85 (m, 1H), 6.72-6.69 (m, 1H), 3.70-3.66 (m, 2H), 3.56 (t, J=6.7 Hz, 2H), 3.37-3.34 (m, 2H), 3.13-3.08 (m, 2H), 2.37-2.33 (m, 2H), 2.22-2.13 (m, 4H), 2.06-2.02 (m, 2H), 1.56-1.50 (m, 2H), 1.47-1.41 (m, 2H), 0.97 (t, J=7.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 157.1, 139.2, 133.2, 130.4, 121.3, 120.7, 117.6, 114.2, 55.3, 54.2, 39.7, 34.3, 32.3, 26.0, 24.1, 23.3, 14.3; HPLC tR=12.3 min (Luna), 97.6%; ES-MS: (M+H)=328 m/z.

Sources & evidence

ORD record
ord-001de229952b423c967dde60d8a1d1a1
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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