HCID 178431023, compound → HCID 178467074, compound

HRID 526120Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]2[NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:18][CH2:17]1.CC1(C)C(C)(C)OB([C:34]2[CH:42]=[CH:41][C:37]3[NH:38][CH:39]=[N:40][C:36]=3[CH:35]=2)O1>>[ClH:1].[ClH:1].[ClH:1].[NH:38]1[C:37]2[CH:41]=[CH:42][C:34]([C:2]3[N:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]4[NH:15][C@H:16]3[CH2:17][CH2:18][C@H:19]([CH2:22][N:23]([CH3:24])[CH3:25])[CH2:20][CH2:21]3)=[CH:35][C:36]=2[N:40]=[CH:39]1

Participants

Reactant 2

HCID 178431023HCID 178431023, compound

HCID 178467145HCID 178467145, compound

Product 1

HCID 178467074HCID 178467074, compoundYield 219.7%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclo-hexylamino}-1,5-naphthyridin-3-yl)ethanone (68 mg, 0.188 mmol) was reacted with 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazole (69 mg, 0.282 mmol) followed by formation of the trihydrochloride salt to afford the desired product (76 mg, 73%) as a yellow-brown solid: 1H NMR (500 MHz, CD3OD) δ 9.49 (s, 1H), 9.19 (s, 1H), 8.63 (d, J=8.9 Hz, 1H), 8.56 (s, 1H), 8.46 (d, J=8.9 Hz, 1H), 8.37 (d, J=8.5 Hz, 1H), 8.19 (d, J=8.5 Hz, 1H), 5.65-5.55 (m, 1H), 3.15 (d, J=6.9 Hz, 2H), 2.93 (s, 6H), 2.78 (s, 3H), 2.52-2.48 (m, 2H), 2.07-1.95 (m, 3H), 1.76-1.64 (m, 2H), 1.43-1.31 (m, 2H); ESI MS m/z 443 [M+H]+; HPLC 97.7% (AUC), tR=8.20 min.

Sources & evidence

ORD record: ord-001bb6c632204300bf4f5a6d66b814ab
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345709B2

Reaction notes

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