Hydrogen Bromide → HCID 86635902, compound

HRID 1987376Notes

Reaction equation

HRID 1987376 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:12]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N:14]=2)[CH2:11][CH2:10][CH2:9][CH:8]1[C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=1.[BrH:29]>CO>[BrH:29].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[CH:12]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N:14]=2)[CH2:11][CH2:10][CH2:9][CH:8]1[C:21]1[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67421361HCID 67421361, compound

Product 1

HCID 86635902HCID 86635902, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl-[4-(3,5,3″,5″-tetramethyl-3′,4′,5′,6′-tetrahydro-2′H-[2,2′;6′,2″]terpyridin-1′-yl)-butyl]-amine (168 mg, 0.440 mmol) in MeOH (1 mL) was added a saturated solution of HBr in MeOH (1 mL) according to General Procedure B. COMPOUND 81 was collected as a white solid (240 mg, 82%). 1H NMR (D2O) δ 1.19-1.31 (m, 4H), 1.46-1.56 (m, 2H), 1.65-1.70 (m, 1H), 1.90-1.95 (m, 1H), 2.11 (d, 2H, J=13.0 Hz), 2.22-2.27 (m, 2H), 2.50 (s, 6H), 2.55 (s, 6H), 2.57 (s, 3H), 2.75-2.81 (m, 2H), 4.53 (d, 2H, J=9.1 Hz), 8.26 (s, 2H), 8.51 (s, 2H); 13C NMR (D2O) δ 16.96, 17.56, 20.05, 22.43, 23.84, 32.65, 32.99, 48.80, 52.14, 57.55, 136.00, 137.42, 139.20, 150.10, 151.69; ES-MS nm/z 381 (M+H). Anal Calcd. For C24H36N4.3.0(HBr).2.1(H2O): C, 43.60; H, 6.59; N, 8.47; Br, 36.26. Found: C, 43.62; H, 6.38; N, 8.15; Br, 36.26.

Workup

  1. customCOMPOUND 81 was collected as a white solid (240 mg, 82%)

Sources & evidence

ORD record
ord-29df65332abb403490ba5c1fba970a53
Source dataset
uspto-grants-2009_06
Patent number
US07550484B2

Reaction notes

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