(2-Isopropoxy-3-methoxy-benzyl)methylamine → (E)-N-(2-Isopropoxy-3-methoxy-benzyl)-N-methyl-3-[4-(3-morpholin-4-yl-propyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylamide hydrochloride

HRID 1362183Notes

Reaction equation

HRID 1362183 reaction equation
[CH:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[CH2:7]CN)([CH3:3])[CH3:2].[CH3:16][NH:17]CC1C=CC2C(=CC=CC=2)C=1CCC.[ClH:32].[N:33]1([CH2:39][CH2:40][CH2:41][N:42]2[CH2:48][C:47]3[CH:49]=[C:50](/[CH:53]=[CH:54]/[C:55]([OH:57])=O)[CH:51]=[N:52][C:46]=3[NH:45][C:44](=[O:58])[CH2:43]2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl.CN1CC2C=C(/C=C/C(O)=O)C=NC=2NC(=O)C1>>[ClH:32].[CH:1]([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[CH2:7][N:17]([CH3:16])[C:55](=[O:57])/[CH:54]=[CH:53]/[C:50]1[CH:51]=[N:52][C:46]2[NH:45][C:44](=[O:58])[CH2:43][N:42]([CH2:41][CH2:40][CH2:39][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[CH2:48][C:47]=2[CH:49]=1)([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 12176049(2-Isopropoxy-3-methoxy-benzyl)methylamineHCID 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 66966377(E)-3-[4-(3-Morpholin-4-yl-propyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylic acid hydrochloride

Product 1

HCID 10054100(E)-N-(2-Isopropoxy-3-methoxy-benzyl)-N-methyl-3-[4-(3-morpholin-4-yl-propyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl]acrylamide hydrochlorideYield 44%

Procedure

According to the procedure of Example 1, except substituting (2-isopropoxy-3-methoxy-benzyl)methylamine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, and substituting (E)-3-[4-(3-morpholin-4-yl-propyl)-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-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 (0.17 g, 44%) was prepared as an off-white powder: 1H NMR (300 MHz, DMSO-d6) δ 11.01 (br s, 1H), 10.66 (br s, 1H), 8.62 (br s, 1H), 8.35-8.22 (m, 1H), 7.57-7.52 (m, 1H), 7.40-7.32 (m, 1H), 7.05-6.93 (m, 2H), 6.66-6.62 (m, 1H), 4.80-4.64 (m, 2H), 4.60-4.45 (m, 1H), 4.08 (br s, 2H), 3.87-3.81 (m, 6H), 3.79 (s, 3H), 3.68 (br s, 2H), 3.50-3.38 (m, 4H), 3.21 (br s, 2H), 3.10-2.72 (m, 3H), 2.01 (br s, 2H), 1.27-1.15 (m, 6H); MS (ESI) m/e 552 (M+H)+.

Sources & evidence

ORD record
ord-64230ee0c9c844ebbdb2783043c0357a
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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