Tetrafluoro-m-phenylenediamine dihydrochloride → HCID 68657306, compound

HRID 930727Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=4)=[CH:13][C:12]3=[O:24])[CH:9]=2)[C:4]2[CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C:3]1=2.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:48].Cl>>[ClH:48].[ClH:48].[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][N:18]=4)=[CH:13][C:12]3=[O:24])[CH:9]=2)[C:4]2[CH2:25][CH2:26][NH:27][CH2:28][C:3]1=2

Participants

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

HCID 70583041HCID 70583041, compound

Product 1

HCID 68657306HCID 68657306, compoundYield 15%

Procedure

tert-Butyl 9-methyl-7-(4-(5-methylpyridin-2-yl)-2-oxopyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (138 mg, 0.27 mmol) was deprotected and converted to the dihydrochloride salt according to the procedure of Example 30 (steps e and g) to provide the title compound (18 mg, 15%) as a yellow solid: mp 303-310° C.; 1H NMR (500 MHz, CD3OD) δ 8.59 (s, 1H), 7.95 (d, J=8.1 Hz, 1H), 7.87 (d, J=6.5 Hz, 1H), 7.80 (d, J=7.0 Hz, 1H), 7.67 (d, J=8.4 Hz, 1H), 7.56 (d, J=1.4 Hz, 1H), 7.24 (d, J=1.6 Hz, 1H), 7.15-7.12 (m, 2H), 4.57 (s, 2H), 3.74 (s, 3H), 3.61 (t, J=6.0 Hz, 2H), 3.14 (t, J=6.1 Hz, 2H), 2.46 (s, 3H); ESI MS m/z 371 [M+H]+; HPLC (Method B)>99% (AUC), tR=11.0 min.

Sources & evidence

ORD record: ord-cee354f435d440379d1387213decd523
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296743B2

Reaction notes

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