Water → HCID 18346789, compound

HRID 1633862Notes

Reaction equation

HRID 1633862 reaction equation
[OH:1][CH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:6]2[CH:19]=[C:20]([C:23]([O:25]C(C)(C)C)=O)[CH:21]=[CH:22][C:5]=2[NH:4]1.[CH3:30][N:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[C:32]1[CH2:40][NH:41][CH3:42].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>>[OH:1][CH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:6]2[CH:19]=[C:20]([C:23]([N:41]([CH3:42])[CH2:40][C:32]3[N:31]([CH3:30])[C:39]4[C:34]([CH:33]=3)=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:25])[CH:21]=[CH:22][C:5]=2[NH:4]1

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 53994421HCID 53994421, compound

Product 1

HCID 18346789HCID 18346789, compoundYield 88.9%

Procedure

According to the procedure of Example 8, except using tert-butyl (2R)-2-hydroxymethyl-3-oxo-4-phenethyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.49 g, 1.2 mmole), 1-methyl-2-(methylaminomethyl)indole (0.23 g, 1.4 mmole), Et3N (0.37 mL, 2.62 mmole), HOBt.H2O (0.19 g, 1.4 mmole), and EDC.HCl (0.27 g, 1.4 mmole), the title compound (0.53 g, 82%) was prepared as an off-white solid following flash chromatography on silica gel (gradient: 1-3% MeOH/CHCl3): MS (ES) m/e 497.1 (M+H)+.

Sources & evidence

ORD record
ord-bedf5040c3b74504ab183ffe8e2aadbb
Source dataset
uspto-grants-2003_01
Patent number
US06503903B1

Reaction notes

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