4-Fluoro-naphthalen-1-ylmethyl-methylamine → (E)-N-(4-Fluoro-naphthalen-1-ylmethyl)-N-methyl-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylamide hydrochloride

HRID 1711919Notes

Reaction equation

HRID 1711919 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][NH:13][CH3:14])=[CH:4][CH:3]=1.CNCC1C=CC2C(=CC=CC=2)C=1CCC.[ClH:31].[N:32]1([CH2:38][CH2:39][N:40]2[CH2:45][C:44]3[CH:46]=[C:47](/[CH:50]=[CH:51]/[C:52]([OH:54])=O)[CH:48]=[N:49][C:43]=3[NH:42][C:41]2=[O:55])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1>>[ClH:31].[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH2:12][N:13]([CH3:14])[C:52](=[O:54])/[CH:51]=[CH:50]/[C:47]2[CH:48]=[N:49][C:43]3[NH:42][C:41](=[O:55])[N:40]([CH2:39][CH2:38][N:32]4[CH2:37][CH2:36][O:35][CH2:34][CH2:33]4)[CH2:45][C:44]=3[CH:46]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 149867704-Fluoro-naphthalen-1-ylmethyl-methylamineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66967508(E)-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylic acid hydrochloride

Product 1

HCID 66967566(E)-N-(4-Fluoro-naphthalen-1-ylmethyl)-N-methyl-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylamide hydrochlorideYield 43%

Procedure

According to the procedure of Example 1, except substituting 4-fluoro-naphthalen-1-ylmethyl-methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-[3-(2-morpholin-4-yl-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]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 (0.13 g, 43%) was prepared as an off-white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.64-10.51 (m, 1H), 10.12 (m, 1H), 8.45-8.30 (m, 1H), 8.22-8.07 (m, 2H), 8.03-7.86 (m, 1H), 7.78-7.62 (m, 2H), 7.63-7.51 (m, 1H), 7.43 (t, J=7.5 Hz, 1H), 7.32 (t, J=8.6 Hz, 1H), 7.21-7.12 (m, 1H), 5.03-5.02 (m, 2H), 4.57-4.42 (m, 2H), 4.01-3.91 (m, 2H), 3.80-3.63 (m, 4H), 3.53-3.43 (m, 2H), 3.40-3.25 (m, 2H), 3.09-2.96 (m, 5H); MS (ESI) m/e 504 (M+H)+.

Sources & evidence

ORD record
ord-2b61a990427f4e2790d10d7bcdfd1d20
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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