Water → HCID 6539884, compound

HRID 1633860Notes

Reaction equation

[CH3:1][N:2]1[CH2:8][C:7]2[CH:9]=[C:10]([C:13]([O:15]C(C)(C)C)=O)[CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][C:3]1=[O:20].[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[CH2:31][NH:32][CH3:33].CCN(CC)CC.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>>[CH3:33][N:32]([CH2:31][C:23]1[N:22]([CH3:21])[C:30]2[C:25]([CH:24]=1)=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]([C:10]1[CH:11]=[CH:12][C:6]2[NH:5][CH2:4][C:3](=[O:20])[N:2]([CH3:1])[CH2:8][C:7]=2[CH:9]=1)=[O:15]

Participants

Reactant 6

HCID 962Water

HCID 8471Triethylamine

HCID 757711-Hydroxybenzotriazole

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

HCID 11087035HCID 11087035, compound

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

Product 1

HCID 6539884HCID 6539884, compoundYield 92%

Procedure

According to the procedure of Example 8, except using tert-butyl 4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-7-carboxylate (0.60 g, 2.2 mmole), 1-methyl-2-(methylaminomethyl)indole (0.35 g, 2.2 mmole), Et3N (0.62 mL, 4,4 mmole), HOBt.H2O (0.30 g, 2.2 mmole), and EDC.HCl (0.42 g, 2.2 mmole), the title compound (0.76 g, 92%) was prepared as an off-white solid following flash chromatography on silica gel (5% MeOH/CHCl3): MS (ES) m/e 377.0 (M+H)+.

Sources & evidence

ORD record: ord-22de51e90ec247f886e490760155e1c4
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503903B1

Reaction notes

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