HCID 25160968, compound → HCID 25160969, compound

HRID 914032Notes

Reaction equation

HRID 914032 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]([F:17])([F:16])[F:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][O:19][CH2:20][C:21]2([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:26][CH2:25][N:24]([C:27](OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH2:3][CH2:2]1.C1(CN2C3C=CC(C4C=CC(C#N)=CC=4)=CC=3N=C2COCC2(C3C=CC=CC=3)CCN(C)CC2)CC1>>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]([F:15])([F:17])[F:16])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:18][O:19][CH2:20][C:21]2([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 25160968HCID 25160968, compoundHCID 57546139HCID 57546139, compound

Product 1

HCID 25160969HCID 25160969, compoundYield 31%

Procedure

N-Methylation of tert-butyl 4-(((1-(cyclopropylmethyl)-5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)methoxy)methyl)-4-phenylpiperidine-1-carboxylate (35 mg, 0.064 mmol) was carried out as described in the preparation of 4-(1-(Cyclopropylmethyl)-2-(((1-methyl-4-phenylpiperidin-4-yl)methoxy)methyl)-1H-benzo[d]imidazol-5-yl)benzonitrile obtain the title compound (9 mg, 31%) as a free base. 1H-NMR (500 MHz, CD3OD) δ 7.93 (s, 1 H), 7.71 (d, J=8.5 Hz, 1 H), 7.60 (d, J=8.5 Hz, 1 H), 7.40-7.25 (m, 5 H), 4.77 (s, 2 H), 3.88 (d, J=6.4 Hz, 2 H), 3.62 (bs, 2 H), 3.41 (m, 2 H), 2.93 (m, 2 H), 2.78 (s, 3 H), 2.54 (m, 2 H), 2.21 (m, 2 H), 1.04 (m, 1 H), 0.53-0.46 (m, 2 H), 0.33-0.29 (m, 2 H). 19F NMR (471 MHz, CD3OD) δ −69.0.

Sources & evidence

ORD record
ord-af5e0c2a597c4a149a88c7a3103170ed
Source dataset
uspto-grants-2011_09
Patent number
US08026257B2

Reaction notes

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