2-(4-(Propan-2-yl)phenyl)ethan-1-amine → (E)-N-(4-Isopropyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamide

HRID 1362167Notes

Reaction equation

HRID 1362167 reaction equation
[CH:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8]CN)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH3:13][NH:14]CC1C=CC2C(=CC=CC=2)C=1CCC.Cl.[O:30]=[C:31]1[NH:40][C:39]2[N:38]=[CH:37][C:36](/[CH:41]=[CH:42]/[C:43]([OH:45])=O)=[CH:35][C:34]=2[CH2:33][CH2:32]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:14]([CH3:13])[C:43](=[O:45])/[CH:42]=[CH:41]/[C:36]2[CH:37]=[N:38][C:39]3[NH:40][C:31](=[O:30])[CH2:32][CH2:33][C:34]=3[CH:35]=2)=[CH:11][CH:12]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 4100822-(4-(Propan-2-yl)phenyl)ethan-1-amineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride

Product 1

HCID 10248153(E)-N-(4-Isopropyl-benzyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylamideYield 61%

Procedure

According to the procedure of Example 1 (a), except substituting (4-isopropyl-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3yl)acrylic acid hydrochloride for the (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride, the title compound (0.223 g, 61%) was prepared as a light orange solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.66-10.64 (m, 1H), 8.36-8.33 (m, 1H), 8.07 (s, 1H), 7.55-7.48 (m, 1H), 7.33-7.11 (m, 5H), 4.77-4.56 (m, 2H), 3.09-2.81 (m, 6H), 2.56-2.49 (m 2H), 1.19-1.16 (m, 6H); MS (APCI) m/e 364 (M+H)+.

Sources & evidence

ORD record
ord-1565ca502eda49a49193fedb4d1708d1
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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