Water → HCID 57021393, compound

HRID 1884540Notes

Reaction equation

HRID 1884540 reaction equation
[CH2:1]([C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[CH2:12][C:11]2[CH:17]=[C:18]([C:21](OC(C)(C)C)=[O:22])[CH:19]=[CH:20][C:10]=2[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[C:30]1[CH2:38][NH:39][CH3:40].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>>[CH2:1]([C@@H:8]1[C:14](=[O:15])[N:13]([CH3:16])[CH2:12][C:11]2[CH:17]=[C:18]([C:21]([N:39]([CH3:40])[CH2:38][C:30]3[N:29]([CH3:28])[C:37]4[C:32]([CH:31]=3)=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:22])[CH:19]=[CH:20][C:10]=2[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 57039089HCID 57039089, compound

Product 1

HCID 57021393HCID 57021393, compoundYield 100%

Procedure

According to the procedure of Example 8, except using tert-butyl (2R)-2-benzyl-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.75 g, 2.1 mmole), 1-methyl-2-(methylaminomethyl)indole (0.34 g, 2.1 mmole), Et3N (0.59 mL, 4.2 mmole), HOBt.H2O (0.28 g, 2.1 mmole), and EDC.HCl (0.41 g, 2.1 mmole), the title compound (0.97 g, 100%) was prepared as an off-white solid following flash chromatography on silica gel (gradient: 80-90% EtOAc/hexanes): MS (ES) m/e 467.1 (M +H)+.

Sources & evidence

ORD record
ord-a663f3a1ed394afcb1b14bf1cbb10add
Source dataset
uspto-grants-2004_07
Patent number
US06765005B2

Reaction notes

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