Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467103, compound

HRID 526084Notes

Reaction equation

HRID 526084 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:39]=[CH:38][C:37]([OH:40])=[C:36]([O:41][C:42]([F:45])([F:44])[F:43])[CH:35]=2)O1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:59].Cl>>[ClH:1].[ClH:59].[CH3:24][N:23]([CH2:22][C@H:19]1[CH2:20][CH2:21][C@H:16]([NH:15][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([O:41][C:42]([F:43])([F:45])[F:44])[CH:35]=4)[N:3]=3)[N:8]=[CH:7][C:6]=2[C:12](=[O:14])[CH3:13])[CH2:17][CH2:18]1)[CH3:25]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 747894824-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenolHCID 178467145HCID 178467145, compound

Product 1

HCID 178467103HCID 178467103, compoundYield 79%

Procedure

Following general procedure II, 1-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexyl amino}-1,5-naphthyridin-3-yl)ethanone (55 mg, 0.15 mmol) was reacted with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethoxy)phenol (68 mg, 0.23 mmol) followed by formation of the dihydrochloride salt to afford the desired product (71 mg, 79%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.45 (d, J=8.9 Hz, 1H), 8.32 (d, J=9.0 Hz, 1H), 8.04-7.97 (m, 2H), 7.21 (d, J=8.6 Hz, 1H), 5.70-5.60 (m, 1H), 3.07 (d, J=6.6 Hz, 2H), 2.94 (s, 6H), 2.76 (s, 3H), 2.50-2.40 (m, 2H), 2.08-1.97 (m, 3H), 1.74-1.62 (m, 2H), 1.39-1.27 (m, 2H). ESI MS m/z 503 [M+H]+; HPLC>99% (AUC), tR=9.80 min.

Sources & evidence

ORD record
ord-42a16b9981454121a17312d331f6d7c0
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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