Water → HCID 53641876, compound

HRID 1633859Notes

Reaction equation

HRID 1633859 reaction equation
[OH:1][CH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH3:11])[CH2:7][C:6]2[CH:12]=[C:13]([C:16]([O:18]C(C)(C)C)=O)[CH:14]=[CH:15][C:5]=2[NH:4]1.[CH3:23][N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25]1[CH2:33][NH:34][CH3:35].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>>[CH3:35][N:34]([CH2:33][C:25]1[N:24]([CH3:23])[C:32]2[C:27]([CH:26]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:16]([C:13]1[CH:14]=[CH:15][C:5]2[NH:4][C@H:3]([CH2:2][OH:1])[C:9](=[O:10])[N:8]([CH3:11])[CH2:7][C:6]=2[CH:12]=1)=[O:18]

Participants

7

Reactant 6

HCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 20742708HCID 20742708, compound

Product 1

HCID 53641876HCID 53641876, compoundYield 91%

Procedure

According to the procedure of Example 8, except using tert-butyl (2R)-2-hydroxymethyl-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.50 g, 1.6 mmole), 1-methyl-2-(methylaminomethyl)indole (0.26 g, 1.6 mmole), Et3N (0.46 mL, 3.3 mmole), HOBt.H2O (0.22 g, 1.6 mmole), and EDC.HCl (0.31 g, 1.6 mmole), the title compound (0.59 g, 91%) was prepared as an off-white solid following flash chromatography on silica gel (gradient: 2-4% MeOH/CHCl3): MS (ES) m/e 407.1 (M+H)+.

Sources & evidence

ORD record
ord-20128d54189649c1974cb7bbe42da330
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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