(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride → HCID 178482617, compound

HRID 2097169Notes

Reaction equation

HRID 2097169 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:11][CH3:12])=[CH:9][C:4]=2[N:3]=[CH:2]1.C(C1C2C(=CC=CC=2)C=CC=1CN)CC.Cl.[O:29]=[C:30]1[NH:39][C:38]2[N:37]=[CH:36][C:35](/[CH:40]=[CH:41]/[C:42]([OH:44])=O)=[CH:34][C:33]=2[CH2:32][CH2:31]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]([CH3:12])[C:42](=[O:44])/[CH:41]=[CH:40]/[C:35]3[CH:36]=[N:37][C:38]4[NH:39][C:30](=[O:29])[CH2:31][CH2:32][C:33]=4[CH:34]=3)=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 4

HCID 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 hydrochlorideHCID 86640777HCID 86640777, compoundHCID 178482615HCID 178482615, compound

Product 1

HCID 178482617HCID 178482617, compoundYield 37%

Procedure

According to the procedure of Example 1 (a), except substituting ((1H-benzo[d]imidazol-5-yl)-N-methylmethanamine) for the methyl-(1-propyl-naphthalen-2-ylmethylamine, and substituting (E)-3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-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. Purification by preparative HPLC (water/acetonitrile/0.05% TFA mixture) gave the title compound ((E)-N-((1H-benzo[d]imidazol-5-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide) (143 mg, 37%) as a white solid and a mixture of amide rotomers: 1H NMR (400 MHz, DMSO-d6) δ 10.60 (m, 1H), 8.36 (m, 1H), 8.21 (s, 1H), 8.07 (s, 1H), 7.59-7.21 (m, 4H), 7.12-7.08 (m, 1H), 4.91-4.72 (m, 2H), 3.10-2.86 (m, 5H), 2.55-2.49 (m, 2H); ESI MS m/z 362 [C20H19N5O2+H]+.

Workup

  1. customPurification by preparative HPLC (water/acetonitrile/0.05% TFA mixture)

Sources & evidence

ORD record
ord-d146dc22ac42421ab8042efe1c8d735e
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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