Lithium Hexamethyldisilazide → HCID 90410491, compound

HRID 1848754Notes

Reaction equation

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

Participants

Reactant 3

HCID 2733832Lithium Hexamethyldisilazide

HCID 27582473,3-Difluoroazetidine hydrochloride

HCID 86268284HCID 86268284, compound

Product 1

HCID 90410491HCID 90410491, compound

Procedure

The title compound was prepared in a manner analogous to that in Example 152 substituting (1R*,2S*)-2-(1-(4-bromobenzyl)-6-((5-methylpyridin-2-yl)methoxy)-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylic acid, 3,3-difluoroazetidine hydrochloride (4 eq), and 5 eq LiHMDS. MS (ESI): mass calcd. for C31H32F2N4O3, 546.24; m/z found, 547.2 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 7.51 (s, 1H), 6.82 (d, J=7.9, 1H), 6.73 (d, J=8.8, 1H), 6.61 (d, J=7.9, 1H), 6.23-6.03 (m, 4H), 5.68 (d, J=8.4, 2H), 4.57 (q, J=16.7, 2H), 4.29 (s, 2H), 3.36 (t, J=11.9, 4H), 2.80-2.70 (m, 1H), 2.10-2.00 (m, 1H), 1.61-1.46 (m, 4H), 1.21-1.13 (m, 1H), 1.12-0.86 (m, 4H), 0.75-0.55 (m, 2H).

Sources & evidence

ORD record: ord-5cfc2cef02f3457684242e8b3775f404
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952177B2

Reaction notes

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