Triethylamine → N5-[1-(3,5-Dimethyl-isoxazol-4-ylmethyl)-pyrrolidin-2-ylmethyl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

HRID 1181293Notes

Reaction equation

HRID 1181293 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7]OS(C)(=O)=O)[CH:3]=1.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]1[N:34]=[C:21]2[N:22]=[C:23]([NH:27][CH2:28][CH:29]3[CH2:33][CH2:32][CH2:31][NH:30]3)[N:24]=[C:25]([NH2:26])[N:20]2[N:19]=1.[CH3:35]CN(CC)CC>CC#N>[CH3:7][C:4]1[C:3]([CH2:35][N:30]2[CH2:31][CH2:32][CH2:33][CH:29]2[CH2:28][NH:27][C:23]2[N:24]=[C:25]([NH2:26])[N:20]3[N:19]=[C:18]([C:14]4[O:13][CH:17]=[CH:16][CH:15]=4)[N:34]=[C:21]3[N:22]=2)=[C:2]([CH3:1])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57476926Methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl esterHCID 694317402-furan-2-yl-N5-pyrrolidin-2-ylmethyl-[1,2,4]-triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Product 1

HCID 11212001N5-[1-(3,5-Dimethyl-isoxazol-4-ylmethyl)-pyrrolidin-2-ylmethyl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulfonic acid 5-methyl-isoxazol-3-ylmethyl ester (48 mg, 0.25 mmol; see Example 2(a) above) was added to a solution of 2-furan-2-yl-N5-pyrrolidin-2-ylmethyl-[1,2,4]-triazolo[1,5-a][1,3,5]triazine-5,7-diamine (0.24 mmol; see Example 6(a) and (b) above) and Et3N (0.30 mmol) in 2 mL of CH3CN. The resulting reaction mixture was stirred at room temperature for 18 hours. It was then concentrated and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1% TFA. 1H NMR (DMSO-d6) δ 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H), 3.8 (br s, 2H), 2.2-3.2 (m, 8H), 1.6 (br s, 6H). MS: m/z: 410 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. concentrationIt was then concentrated
  3. custompurified by preparative HPLC
  4. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-ac291698263340f6b79f3eec54d9f90b
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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