Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 68657856, compound

HRID 1020600Notes

Reaction equation

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

Participants

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 44193892ALB-127158

Product 1

HCID 68657856HCID 68657856, compoundYield 78%

Procedure

4-((5-Fluoropyridin-2-yl)methoxy)-1-(5-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-7-yl)pyridin-2(1H)-one (75 mg, 0.19 mmol) was reacted according to the procedure of Example 47 to provide the free-base. Conversion to the dihydrochloride salt using the procedure of Example 30 (step g) provided the title compound (71 mg, 78%) as a white solid: mp 215-230° C.; 1H NMR (500 MHz, CD3OD) δ 8.65 (d, J=2.6 Hz, 1H), 7.91 (overlapping ddd, J=9.6, 2.1 Hz, 1H), 7.83-7.20 (m, 2H), 7.61 (d, J=8.4 Hz, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.09 (dd, J=8.4, 1.8 Hz, 1H), 6.59 (dd, J=7.5, 2.6 Hz, 1H), 6.36 (d, J=2.6 Hz, 1H), 5.41 (s, 2H), 4.76 (d, J=14.2 Hz, 1H), 4.39 (d, J=14.2 Hz, 1H), 3.94-3.82 (m, 2H), 3.74 (s, 3H), 3.65-3.58 (m, 2H), 3.13 (s, 3H); ESI MS m/z 419 [M+H]+; HPLC (Method B) 95.8% (AUC), tR=110 min.

Workup

customto provide the free-base

Sources & evidence

ORD record: ord-7717d6a5d7874e01be8c210e38f679a7
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716308B2

Reaction notes

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