N-[(3,4-dichlorophenyl)methyl]cyclopropanamine → HCID 90407145, compound

HRID 2277528Notes

Reaction equation

HRID 2277528 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([O:21]C)=[O:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1)(=O)=O.[Cl:23][C:24]1[CH:25]=[C:26]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:27][NH:28][CH:29]1[CH2:31][CH2:30]1>>[CH:29]1([N:28]([CH2:27][C:26]2[CH:32]=[CH:33][C:34]([Cl:35])=[C:24]([Cl:23])[CH:25]=2)[CH2:6][CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][N:14]=3)[N:10]=[CH:9]2)[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 4719898N-[(3,4-dichlorophenyl)methyl]cyclopropanamineHCID 90407071methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate

Product 1

HCID 90407145HCID 90407145, compoundYield 7%

Procedure

The title compound was prepared in 7% yield from methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 6) and (3,4-dichlorobenzyl)cyclopropylamine according to the procedure for the preparation of Example 58. 1HNMR (400 MHz, DMSO): δ 0.14 (2H, m), 0.40 (2H, m), 1.85 (1H, m), 2.90 (2H, t, J=6.2 Hz), 3.74 (2H, s), 4.14 (2H, t, J=6.2 Hz), 7.21 (1H, dd, J=8.3 and 1.8 Hz), 7.45-7.56 (3H, m), 7.70 (1H, s), 7.72 (1H, s), 8.26 (1H, s), 8.56 (1H, d). [M+H] Calc'd for C21H20Cl2N4O2, 432. Found, 432.

Sources & evidence

ORD record
ord-309a7304a04c432eabd66b3dcd4c7fd0
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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