Ammonia → HCID 53839542, compound

HRID 582555Notes

Reaction equation

HRID 582555 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][CH:30]=[CH:29][CH:28]=3)[CH2:25]O)[CH2:20][CH2:19]2)[CH:5]=1.C([N:35](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][CH:30]=[CH:29][CH:28]=3)[CH2:25][NH2:35])[CH2:20][CH2:19]2)[CH:5]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 10788768HCID 10788768, compound

Product 1

HCID 53839542HCID 53839542, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In the same way as that described in Example 7, Step 1 using 1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]-4-[2-hydroxy-1-phenylethyl]piperazine (330 mg, 0.77 mmol), triethylamine (214 μL, 1.53 mmol), methanesulphonyl chloride (118 μL, 1.53 mmol) and THF (15 mL). The crude mesylate was then reacted with ammonia (7.7 mL of a 2.0M solution in MeOH, 15.3 mmol) in the same way as that described in Example 7, Step 1. The amine (185 mg, 56%) was isolated as a pale yellow foam. 1H NMR (250 MHz, CDCl3) δ1.88-2.00 (2H, m), 2.38-2.76 (12H, m), 2.79 (2H, t, J=7.5 Hz), 4.11 (1H, dd, J=10.4 and 3.6 Hz), 7.13-7.18 (2H, m), 7.22-7.39 (5H, m), 7.47 (1H, d, J=8.6 Hz), 7.59 (1H, s), 8.34 (1H, br s), 8.46 (2H, s). MS (430, M+1).

Sources & evidence

ORD record
ord-a4e35de670af4023abfe9d40633d8b26
Source dataset
uspto-grants-1999_07
Patent number
US05925638

Reaction notes

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