Methyl-(1-propyl-naphthalen-2-ylmethyl)amine → (E)-N-Acenaphthen-5-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 1711905Notes

Reaction equation

HRID 1711905 reaction equation
[ClH:1].[N:2]1([CH2:8][CH2:9][N:10]2[CH2:15][C:14]3[CH:16]=[C:17](/[CH:20]=[CH:21]/[C:22]([OH:24])=O)[CH:18]=[N:19][C:13]=3[NH:12][C:11]2=[O:25])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1.[CH2:45]1[C:55]2=[C:56]3[C:51](=[CH:52][CH:53]=[CH:54]2)[C:50]([CH2:57][NH:58][CH3:59])=[CH:49][CH:48]=[C:47]3[CH2:46]1.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[ClH:1].[CH2:45]1[C:55]2=[C:56]3[C:51](=[CH:52][CH:53]=[CH:54]2)[C:50]([CH2:57][N:58]([CH3:59])[C:22](=[O:24])/[CH:21]=[CH:20]/[C:17]2[CH:18]=[N:19][C:13]4[NH:12][C:11](=[O:25])[N:10]([CH2:9][CH2:8][N:2]5[CH2:7][CH2:6][O:5][CH2:4][CH2:3]5)[CH2:15][C:14]=4[CH:16]=2)=[CH:49][CH:48]=[C:47]3[CH2:46]1

Participants

5

Reactant 4

HCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochlorideHCID 669671841-(1,2-Dihydroacenaphthylen-5-yl)-N-methylmethanamineHCID 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 66966955(E)-N-Acenaphthen-5-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 (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, and substituting acenaphthen-5-ylmethyl-methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (175 mg, 43%) was prepared as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 10.15-10.11 (m, 2H), 8.41-8.33 (m, 1H), 7.98-7.96 (m, 1H), 7.88-7.74 (m, 1H), 7.60-7.44 (m, 2H), 7.38-7.12 (m, 4H), 5.23-5.01 (m, 2H), 4.55-4.46 (m, 2H), 4.00-3.96 (m, 2H), 3.86-3.36 (m, 10H), 3.12-2.89 (m, 7H); MS (ESI) m/e 512 (M+H)+.

Sources & evidence

ORD record
ord-77c35dc49be542c8a2e2aa3c70f0f24f
Source dataset
uspto-grants-2010_09
Patent number
US07790709B2

Reaction notes

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