Tetrafluoro-m-phenylenediamine dihydrochloride → 2,6-Dichloro-4-(8-{4-[(dimethylamino)methyl]phenylamino}-7-(methylsulfonyl)-1,5-naphthyridin-2-yl)phenol dihydrochloride

HRID 526089Notes

Reaction equation

HRID 526089 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]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]2[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=1.[Cl:27][C:28]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:27].[Cl:27][C:28]1[CH:33]=[C:32]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([NH:16][C:17]4[CH:22]=[CH:21][C:20]([CH2:23][N:24]([CH3:26])[CH3:25])=[CH:19][CH:18]=4)[C:6]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:7][N:8]=3)[N:3]=2)[CH:31]=[C:30]([Cl:43])[C:29]=1[OH:44]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 667151272,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 1177740676-chloro-N-{4-[(dimethylamino)methyl]phenyl}-3-(methylsulfonyl)-1,5-naphthyridin-4-amine

Product 1

HCID 1369271952,6-Dichloro-4-(8-{4-[(dimethylamino)methyl]phenylamino}-7-(methylsulfonyl)-1,5-naphthyridin-2-yl)phenol dihydrochlorideYield 56.5%

Procedure

Following general procedure II, 6-chloro-N-{4-[(dimethylamino)methyl]phenyl}-3-(methylsulfonyl)-1,5-naphthyridin-4-amine (50 mg, 0.14 mmol) was reacted with 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (61 mg, 0.21 mmol) followed by formation of the dihydrochloride salt to afford the desired product (35 mg, 42%) as an orange solid: 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 8.47 (d, J=9.1 Hz, 1H), 8.38 (d, J=9.2 Hz, 1H), 7.63 (d, J=9.0 Hz, 2H), 7.59-7.52 (m, 2H), 7.34 (s, 2H), 4.43 (s, 2H), 3.48 (s, 3H), 2.86 (s, 6H); ESI MS m/z 517 [M+H]+; HPLC>99% (AUC), tR=11.03 min.

Sources & evidence

ORD record
ord-4948b03baa174dc0b6d20d4efc528369
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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