Hydrochloric Acid → (E)-1-(3-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one hydrochloride

HRID 1162120Notes

Reaction equation

HRID 1162120 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][C:16]3=[O:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH:21](/B(O)O)=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26].[ClH:30]>CCOCC>[ClH:30].[CH:21](/[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][C:16]3=[O:20])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1)=[CH:22]\[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 5326225B-(1E)-1-Hexenylboronic acidHCID 686481591-(3-(3-Bromoimidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one

Product 1

HCID 68648540(E)-1-(3-(3-(Hex-1-enyl)imidazo[1,2-b]pyridazin-6-ylamino)propyl)pyrrolidin-2-one hydrochlorideYield 52%

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 (68 mg, 52%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 7.90 (s, 1H), 7.86 (d, J=9.8 Hz, 1H), 7.16 (d, J=9.8 Hz, 1H), 6.89 (dt, J=6.1, 16.2 Hz, 1H), 6.68 (d, J=16.2 Hz, 1H), 3.50 (t, J=7.0 Hz, 2H), 3.44-3.40 (m, 4H), 2.38-2.32 (m, 4H), 2.09-2.03 (m, 2H), 1.98-1.93 (m, 2H), 1.56-1.50 (m, 2H), 1.46-1.40 (m, 2H), 0.98-0.96 (t, J=6.3 Hz, 3H); 13C NMR (125 MHz, CD3OD) δ 177.8, 157.1, 139.0, 133.3, 130.1, 121.2, 120.6, 117.9, 114.3, 41.3, 39.9, 34.3, 32.4, 32.1, 26.9, 23.3, 18.9, 14.3 (one signal overlapping with solvent); HPLC tR=11.4 min (Luna), 97.3%; ES-MS: (M+H)=342 m/z.

Sources & evidence

ORD record
ord-72f588abc48d4dc18217dcbdf87d7cfe
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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