3,3-Difluoropiperidine → HCID 90410523, compound

HRID 1848753Notes

Reaction equation

HRID 1848753 reaction equation
Br[C:2]1[CH:34]=[CH:33][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[C:13]([O:16][CH2:17][C:18]4[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=4)[CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[CH2:24][C:25]([CH2:31][CH3:32])([CH2:29][CH3:30])[C:26]([OH:28])=[O:27])=[CH:4][CH:3]=1.[F:35][C:36]1([F:42])[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1>>[F:35][C:36]1([F:42])[CH2:41][CH2:40][CH2:39][N:38]([C:2]2[CH:34]=[CH:33][C:5]([CH2:6][N:7]3[C:11]4[CH:12]=[C:13]([O:16][CH2:17][C:18]5[CH:22]=[CH:21][N:20]([CH3:23])[N:19]=5)[CH:14]=[CH:15][C:10]=4[N:9]=[C:8]3[CH2:24][C:25]([CH2:31][CH3:32])([CH2:29][CH3:30])[C:26]([OH:28])=[O:27])=[CH:4][CH:3]=2)[CH2:37]1

Participants

3

Reactant 2

HCID 27583503,3-DifluoropiperidineHCID 90410891HCID 90410891, compound

Product 1

HCID 90410523HCID 90410523, compound

Procedure

The title compound was prepared using analogous conditions described in Example 152 using 2-((1-(4-bromobenzyl)-6-((1-methyl-1H-pyrazol-3-yl)methoxy)-1H-benzo[d]imidazol-2-yl)methyl)-2-ethylbutanoic acid and 3,3-difluoropiperidine. MS (ESI): mass calcd. for C31H37F2N5O3, 565.2; m/z found, 566.3 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=9.0, 1H), 7.57-7.51 (m, 1H), 7.34 (d, J=2.1, 1H), 7.25 (dd, J=9.1, 2.3, 1H), 7.13 (d, J=8.7, 2H), 6.96 (d, J=8.8, 2H), 6.28 (d, J=2.2, 1H), 6.25 (d, J=2.2, OH), 5.65 (s, 2H), 5.07 (s, 2H), 3.84 (s, 3H), 3.40 (t, J=5.7, 4H), 3.27-3.23 (m, 2H), 2.08-1.96 (m, 2H), 1.89-1.68 (m, 6H), 0.90-0.83 (m, 6H).

Sources & evidence

ORD record
ord-e4ffa2f0360944c9a87880438c00e347
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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