Tetrafluoro-m-phenylenediamine dihydrochloride → 1-(5-Methyl-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indol-7-yl)-4-(6-methylpyridin-3-yl)pyridin-2(1h)-one dihydrochloride

HRID 1020649Notes

Reaction equation

HRID 1020649 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:24])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27][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[CH:9]=[C:8]([N:11]3[CH:16]=[CH:15][C:14]([C:17]4[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=4)=[CH:13][C:12]3=[O:24])[CH:7]=[CH:6][C:5]=2[C:4]2[CH2:25][NH:26][CH2:27][CH2:28][C:3]1=2

Participants

3

Reactant 2

HCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86635685tert-Butyl 5-methyl-7-(4-(6-methylpyridin-3-yl)-2-oxopyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

Product 1

HCID 686572451-(5-Methyl-2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indol-7-yl)-4-(6-methylpyridin-3-yl)pyridin-2(1h)-one dihydrochlorideYield 29%

Procedure

tert-Butyl 5-methyl-7-(4-(6-methylpyridin-3-yl)-2-oxopyridin-1(2H)-yl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (220 mg, 0.47 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 (50.2 mg, 29%) as a yellow solid: mp 295-305° C.;

Sources & evidence

ORD record
ord-b6310866fc6c494f91012e629ab1c8ac
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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