2-Butene, 1-bromo-3-methyl- → HCID 131724541, compound

HRID 1836583Notes

Reaction equation

HRID 1836583 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].[ClH:7].Cl.[CH:9]1[CH:18]=[CH:17][C:16]2[CH2:19][CH2:20][CH2:21][N:14]3[C:15]=2[C:10]=1[C@H:11]1[CH2:24][NH:23][CH2:22][C@H:12]1[CH2:13]3>>[ClH:7].[ClH:7].[CH3:5][C:4]([CH3:6])=[CH:3][CH2:2][N:23]1[CH2:24][C@H:11]2[C@H:12]([CH2:13][N:14]3[CH2:21][CH2:20][CH2:19][C:16]4[CH:17]=[CH:18][CH:9]=[C:10]2[C:15]3=4)[CH2:22]1

Participants

3

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 131724533HCID 131724533, compound

Product 1

HCID 131724541HCID 131724541, compound

Procedure

Using 4-bromo-2-methyl-2-butene and following the procedures described in EXAMPLE 104, (±)-cis-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline free base from EXAMPLE 11 was converted into the title compound of EXAMPLE 106 as an off-white powder. 1H NMR (dmso-D6) δ: 11.05 (broad s, 1H), 6.86 (t, 1H, J=6.2 Hz), 6.81 (t, 1H, J=7.0 Hz), 6.59 (q, 1H, J=7.3 Hz), 5.33-5.27 (m, 1H), 3.90-3.60 (m, 4H), 3.50-3.25 (m, 2H), 3.10-2.95 (m, 3H), 2.90-2.75 (m, 3H), 2.72-2.65 (m, 2H), 1.95-1.85 (m, 2H), 1.72 (s, 3H), 1.64 (s, 3H). LRMS (ES)+: 283.2 (M+H)+.

Sources & evidence

ORD record
ord-08565eacb31f4316a09a3d2a7d536573
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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