1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-((R)-2-methyl-2,3-dihydroindol-1-yl)-2-(1-methyl-4-morpholin-4-yl-6-thioxo-1,6-dihydropyrimidin-2-yl)ethanone

HRID 2278673Notes

Reaction equation

HRID 2278673 reaction equation
[CH3:1][N:2]1[C:7](=[S:8])[CH:6]=[C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:4]=[C:3]1[CH2:15][C:16]([O-:18])=O.[Na+].Cl.CN(C)CCCN=C=NCC.[CH3:32][C@@H:33]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34]1>CN(C=O)C.N1C=CC=CC=1>[CH3:32][C@@H:33]1[CH2:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]1[C:16](=[O:18])[CH2:15][C:3]1[N:2]([CH3:1])[C:7](=[S:8])[CH:6]=[C:5]([N:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)[N:4]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6999618(2R)-2-methyl-2,3-dihydro-1H-indoleHCID 86699290Sodium (1-methyl-4-morpholin-4-yl-6-thioxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 866992891-((R)-2-methyl-2,3-dihydroindol-1-yl)-2-(1-methyl-4-morpholin-4-yl-6-thioxo-1,6-dihydropyrimidin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

The product is prepared by following the procedure described in example 4e (step 4e) using 250 mg of sodium (1-methyl-4-morpholin-4-yl-6-thioxo-1,6-dihydropyrimidin-2-yl)acetate in 6 ml of DMF and 6 ml of pyridine are added 512 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 126 mg of (R)-2-methyl-2,3-dihydro-1H-indole (which can be prepared according to Krasnov, V. P. et al. (Mendeleev Commun. 2002, 12(1), 27-28)).

Workup

  1. customThe product is prepared

Sources & evidence

ORD record
ord-94d8a5564163474eb62677e232fa92b9
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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