2,3-Dihydro-N-methyl-1H-indene-5-methanamine → HCID 10451243, compound

HRID 1362168Notes

Reaction equation

HRID 1362168 reaction equation
C1C2C(=CC(CNC)=CC=2)CC1.[CH3:13][NH:14][CH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=C[CH:20]=[CH:21][CH:22]=2)[C:17]=1CCC.Cl.[O:30]=[C:31]1[NH:40][C:39]2[N:38]=[CH:37][C:36](/[CH:41]=[CH:42]/[C:43](O)=[O:44])=[CH:35][C:34]=2[CH2:33][CH2:32]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH2:22]1[C:23]2[C:24](=[CH:25][C:16]([CH2:15][N:14]([CH3:13])[C:43](=[O:44])/[CH:42]=[CH:41]/[C:36]3[CH:37]=[N:38][C:39]4[NH:40][C:31](=[O:30])[CH2:32][CH2:33][C:34]=4[CH:35]=3)=[CH:17][CH:18]=2)[CH2:20][CH2:21]1

Participants

5

Reactant 4

HCID 431636802,3-Dihydro-N-methyl-1H-indene-5-methanamineHCID 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 10451243HCID 10451243, compoundYield 45%

Procedure

According to the procedure of Example 1 (a), except substituting indan-5-ylmethyl-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 (0.232 g, 45%) was prepared as an off-white 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), 8.07-8.06 (m, 1H), 7.54-7.49 (m, 1H), 7.33-6.89 (m, 4H), 4.75-4.56 (m, 2H), 3.07-2.72 (m, 9H), 2.53-2.49 (m, 2H), 2.04-1.94 (m 2H); MS (APCI) m/e 362 (M+H)+.

Sources & evidence

ORD record
ord-fd554ce1b40f4c2f9b8ce74796c04fe6
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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