N,N-Dimethyl-1,3-propanediamine → HCID 67300508, compound

HRID 1015453Notes

Reaction equation

HRID 1015453 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=O)=[CH:13][CH:14]=3)[C:9]([CH3:19])=[C:8]2[CH3:20])=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][NH2:28].ON1C2C=CC=CC=2N=N1.N=C=N.[N-]=C=O>CN(C)C=O.C(N(CC)CC)C>[CH3:23][N:24]([CH3:29])[CH2:25][CH2:26][CH2:27][NH:28][C:16]([C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:22][CH:21]=1)[C:8]([CH3:20])=[C:9]2[CH3:19])=[O:18]

Participants

8

Reactant 5

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 757711-HydroxybenzotriazoleHCID 105034IsocyanateHCID 160435Carbodiimide2×HCID 67300384HCID 67300384, compound

Product 1

HCID 67300508HCID 67300508, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A 8.9 mg portion of 1-(4-fluorobenzyl)-2,3-dimethyl-1H-indole-5-carboxylic acid, 3.1 mg of N,N-dimethylpropane-1,3-diamine, 4.1 mg of 1-hydroxybenzotriazole (HOBt) and 0.0083 ml of triethylamine were dissolved in 1.0 ml of N,N-dimethylformamide, and 100 mg of PS-Carbodiimide (Argonaut Technologies, Inc., USA) was added, followed by overnight stirring at room temperature. Then, 50 mg of MP-Carbodiimide (Argonaut Technologies, Inc., USA) and 50 mg of PS-Isocyanate (Argonaut Technologies, Inc., USA) was added to the reaction liquid at room temperature, followed by stirring for 4 hours. Then, the reaction liquid was filtered. By concentrating the filtrate under a reduced pressure, 9.5 mg of N-[3-(dimethylamino)propyl]-(4-fluorobenzyl)-2,3-dimethyl-1H-indole-5-carboxamide was obtained.

Workup

  1. stirringby stirring for 4 hours
  2. customThen, the reaction liquid
  3. filtrationwas filtered
  4. concentrationBy concentrating the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-7f86865abcd54974b2b5fabb58d9e290
Source dataset
uspto-grants-2011_07
Patent number
US07985764B2

Reaction notes

Loading…