Ammonia → HCID 54184040, compound

HRID 582552Notes

Reaction equation

HRID 582552 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:25]O)[CH2:20][CH2:19]2)[CH:5]=1.C([N:36](CC)CC)C.CS(Cl)(=O)=O.S([O-])(=O)(=O)C.N>CO.C1COCC1>[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([CH:24]([C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)[CH2:25][NH2:36])[CH2:20][CH2:19]2)[CH:5]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 9868294HCID 9868294, compound

Product 1

HCID 54184040HCID 54184040, compoundYield 53.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the same way as that described in Example 6 using 1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]-4-[1-(4-fluorophenyl)-2-hydroxyethyl]piperazine (113 mg, 0.25 mmol), triethylamine (70 μL, 0.50 mmol), methanesulphonyl chloride (39 μL, 0.50 mmol) and THF (5 mL). The crude mesylate was converted to the amine in the same manner as that used in Example 6, using ammonia (2.5 mL of a 2M solution in MeOH, 5.0 mmol). The amine (60 mg, 53%) was isolated as a pale yellow foam. 1H NMR (250 MHz, CDCl3) δ1.89-2.01 (2H, m), 2.27-2.85 (14H, m), 4.10 (1H, dd, J=10.1 and 3.8 Hz), 7.00 (2H, dd, JHA-HB =8.7 Hz and JHA-F =8.7 Hz), 7.13-7.16 (2H, m), 7.34 (2H, dd, JHB-HA =8.7 Hz and JHB-F =5.5 Hz), 7.47 (1H, d, J=8.6 Hz), 7.57 (1H, d, J=1.9 Hz), 8.37 (1H, br s), 8.47 (2H, s). MS (ES+) (448, M+1).

Sources & evidence

ORD record
ord-f6895e8db5c3464facda07cc433fa30e
Source dataset
uspto-grants-1999_07
Patent number
US05925638

Reaction notes

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