Dimethylamine → HCID 70009263, compound

HRID 1266032Notes

Reaction equation

HRID 1266032 reaction equation
N1(CCO[C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:20]4[CH2:21][CH2:22][C:23]5[NH:24][C:25](=[O:28])[CH:26]=[CH:27][C:18]([C:19]=54)=[CH:17][N:16]=3)=[CH:11][CH:10]=2)CCCC1.OCCC1C=CC([C:38]2[N:43]3[CH2:44]CC4NC(=O)C=C[C:41]([C:42]=43)=CN=2)=CC=1.CNC.N.C(Cl)(Cl)Cl.[K+].[Br-]>>[CH3:38][N:43]([CH3:44])[CH2:42][CH2:41][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:20]3[CH2:21][CH2:22][C:23]4[NH:24][C:25](=[O:28])[CH:26]=[CH:27][C:18]([C:19]=43)=[CH:17][N:16]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 5

HCID 674DimethylamineHCID 253877Potassium BromideHCID 69701305HCID 69701305, compoundHCID 69701358HCID 69701358, compoundHCID 86758924HCID 86758924, compound

Product 1

HCID 70009263HCID 70009263, compoundYield 26%

Procedure

The product was prepared following the procedure used for 1-[4-(2-Pyrrolidin-1-yl-ethoxy)-phenyl]-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one (Example 123) from 1-[4-(2-hydroxy-ethyl)-phenyl]-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one (Example 127) and methanolic dimethylamine heating to 85° C. overnight to give a 26% yield (2 steps) of a yellow solid: mp >98° C. (dec); Rf=0.08 (7% methanolic ammonia/CHCl3); IR (KBr) 1653, 1479, 1381, 1307 cm−1; 1H NMR (DMSO-d6) δ 2.21 (s, 6H), 2.50-2.56 (m, 2H), 2.79-2.84 (m, 2H), 3.52-3.53 (m, 2H), 4.44-4.46 (m, 2H), 7.34 (t, 1H, J=7.8 Hz), 7.43 (d, 2H, J=8.2 Hz), 7.77 (d, 2H, J=8.2 Hz), 7.84-7.90 (m, 2H), 8.39-8.43 (m, 1H). HRMS calcd for C20H23N4O 335.1872 (M+H), found 335.1865. Anal. (C20H22N4O) C, H, N.

Workup

  1. customThe product was prepared
  2. customto give a 26% yield (2 steps) of a yellow solid

Sources & evidence

ORD record
ord-bd2a82b396594c0ab21b0d8c0db3f246
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

Loading…