Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 178467114, compound

HRID 2178846Notes

Reaction equation

HRID 2178846 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]2[CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:18][CH2:17]1.[Cl:28][C:29]1[CH:34]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:32]=[C:31]([F:44])[C:30]=1[OH:45].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[ClH:1].[ClH:28].[Cl:28][C:29]1[CH:34]=[C:33]([C:2]2[N:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:12](=[O:14])[CH3:13])=[C:5]3[NH:15][C@H:16]2[CH2:17][CH2:18][C@H:19]([CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:20][CH2:21]2)[CH:32]=[C:31]([F:44])[C:30]=1[OH:45]

Participants

4

Reactant 3

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 667160792-Chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 178467140HCID 178467140, compound

Product 1

HCID 178467114HCID 178467114, compoundYield 79.8%

Procedure

Following general procedure II, 1-(6-chloro-4-{[trans-4-(pyrrolidin-1-ylmethyl)-cyclohexyl]amino}-1,5-naphthyridin-3-yl)ethanone (86 mg, 0.22 mmol) was reacted with 2-chloro-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (90 mg, 0.33 mmol) followed by formation of the dihydrochloride salt to afford the desired product (75 mg, 69%) as a light brown solid: 1H NMR (500 MHz, CD3OD) δ 9.14 (s, 1H), 8.45 (d, J=9.0 Hz, 1H), 8.34 (d, J=9.0 Hz, 1H), 8.02 (s, 1H), 7.88 (dd, J=11.5, 2.0 Hz, 1H), 5.74-5.64 (m, 1H), 3.74-3.68 (m, 2H), 3.18-3.10 (m, 4H), 2.76 (s, 3H), 2.47-2.41 (m, 2H), 2.22-1.98 (m, 7H), 1.74-1.62 (m, 2H), 1.47-1.34 (m, 2H); ESI MS m/z 497 [M+H]+; HPLC 96.6% (AUC), tR=9.90 min.

Sources & evidence

ORD record
ord-f3264c97551144aa87bbb087bfbf4d7b
Source dataset
uspto-grants-2015_06
Patent number
US09067937B2

Reaction notes

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