N-[(4-fluorophenyl)methyl]cyclopropanamine → HCID 85470886, compound

HRID 2277514Notes

Reaction equation

HRID 2277514 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.[F:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][NH:31][CH:32]2[CH2:34][CH2:33]2)=[CH:26][CH:25]=1>>[CH:32]1([N:31]([CH2:30][C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=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)[CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 573031N-[(4-fluorophenyl)methyl]cyclopropanamineHCID 90407071methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate

Product 1

HCID 85470886HCID 85470886, compoundYield 9%

Procedure

The title compound was prepared in 9% yield from methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 6) and N-[(4-fluorophenyl)methyl]cyclopropylamine according to the procedure for the preparation of Example 58. 1HNMR (400 MHz, DMSO): δ 0.16 (2H, m), 0.39 (2H, m), 1.82 (1H, m), 2.87 (2H, t, J=6.4 Hz), 3.74 (2H, s), 4.10 (2H, t, J=6.2 Hz), 7.09 (2H, t, J=8.9 Hz), 7.28 (2H, dd, J=7.1 Hz and 2.7 Hz), 7.51 (1H, d, J=4.5 Hz), 7.67 (2H, d, J=1.6 Hz), 8.25 (1H, s), 8.47 (1H, d, J=4.8 Hz). [M+H] Calc'd for C21H21FN4O2, 381. Found, 381.

Sources & evidence

ORD record
ord-4acfceea301642739d2fa4e0299176fc
Source dataset
uspto-grants-2015_09
Patent number
US09133166B2

Reaction notes

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