N-Methylbenzylamine → HCID 9996182, compound

HRID 1362170Notes

Reaction equation

HRID 1362170 reaction equation
C(NC)C1C=CC=CC=1.[CH3:10][NH:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=CC=CC=2)[C:14]=1CCC.Cl.[O:27]=[C:28]1[NH:37][C:36]2[N:35]=[CH:34][C:33](/[CH:38]=[CH:39]/[C:40](O)=[O:41])=[CH:32][C:31]=2[CH2:30][CH2:29]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[CH2:12]([N:11]([CH3:10])[C:40](=[O:41])/[CH:39]=[CH:38]/[C:33]1[CH:34]=[N:35][C:36]2[NH:37][C:28](=[O:27])[CH2:29][CH2:30][C:31]=2[CH:32]=1)[C:13]1[CH:14]=[CH:15][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 7669N-MethylbenzylamineHCID 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 9996182HCID 9996182, compoundYield 93%

Procedure

According to the procedure of Example 1 (a), except substituting 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-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, the title compound (0.462 g, 93%) was prepared as an off-white solid and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 10.64 (s, 1H), 8.37-8.33 (m, 1H), 8.08-8.06 (m, 1H), 7.54-7.49 (m, 1H), 7.37-7.21 (m, 6H), 4.82-4.61 (m, 2H), 3.10-2.85 (m, 5H), 2.56-2.49 (m, 2H); MS (APCI) m/e 322 (M+H)+.

Sources & evidence

ORD record
ord-f04e0ce6d0424b7ab862a89423a6a4d5
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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