Hydrochloric Acid → 6-(2,4-Difluorophenyl)-2-methyl-N-(1,2,3,4-tetrahydroquinolin-7-yl)nicotinamide

HRID 494293

Reaction equation

HRID 494293 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][N:9]2C(=O)C(F)(F)F)=[CH:4][CH:3]=1.[CH3:18][C:19]1[N:27]=[C:26]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])[CH:25]=[CH:24][C:20]=1[C:21](O)=[O:22].Cl>>[F:35][C:29]1[CH:30]=[C:31]([F:34])[CH:32]=[CH:33][C:28]=1[C:26]1[CH:25]=[CH:24][C:20]([C:21]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH2:7][CH2:8][NH:9]3)=[CH:4][CH:3]=2)=[O:22])=[C:19]([CH3:18])[N:27]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 69042733HCID 69042733, compoundHCID 820484221-(7-Amino-3,4-dihydroquinolin-1(2H)-yl)-2,2,2-trifluoroethanone

Product 1

HCID 576827176-(2,4-Difluorophenyl)-2-methyl-N-(1,2,3,4-tetrahydroquinolin-7-yl)nicotinamide

Procedure

Using the procedure outlined in Example 38, the title compound was prepared from 7-amino-1-trifluoroacetyl-1,2,3,4-tetrahydroquinoline (D5) (73 mg, 0.30 mmol) and 2-methyl-6-(2,4-difluorophenyl)nicotinic acid (D106) (82 mg, 0.33 mmol) then converted to the HCl salt as an off-white solid. 1H NMR (400 MHz, MeOH-d4) δ (ppm): 8.46 (d, 1H), 8.11 (d, 1H), 7.93-8.01 (m, 2H), 7.81 (d, 1H), 7.40 (d, 1H), 7.25 (m, 2H), 3.55 (m, 2H), 2.96 (t, 2H), 2.88 (s, 3H), 2.18 (m, 2H).

Sources & evidence

ORD record
ord-e106e82d9375402dbc447aef1705df09
Source dataset
uspto-grants-2009_05
Patent number
US07538121B2

Linked notes

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