Triethylamine → HCID 69432731, compound

HRID 1181295Notes

Reaction equation

HRID 1181295 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[N:9]1([C:16]2[N:21]=[C:20]([NH2:22])[N:19]3[N:23]=[C:24]([C:26]4[O:27][CH:28]=[CH:29][CH:30]=4)[N:25]=[C:18]3[N:17]=2)[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.CCN(CC)CC>CC#N>[O:27]1[CH:28]=[CH:29][CH:30]=[C:26]1[C:24]1[N:25]=[C:18]2[N:17]=[C:16]([N:9]3[CH2:15][CH2:14][CH2:13][N:12]([CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=4)[CH2:11][CH2:10]3)[N:21]=[C:20]([NH2:22])[N:19]2[N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23393Picolyl chlorideHCID 69431799HCID 69431799, compound

Product 1

HCID 69432731HCID 69432731, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Chloromethyl-pyridine (1.5 eq.) was directly added to a solution of 5-[1,4]diazepan-1-yl-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.14 mmol; see Example 8(a) above) and Et3N (0.3 mmol) in 3 mL of CH3CN. The resulting reaction mixture was stirred at room temp 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 (DMMSO-d6) δ 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 6.9-7.1 (m, 4H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H); 3.8 (br s, 2H), 2.2-3.2 (m, 10 H). MS: m/z: 392 [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-3a240de4e1b34c0fb0d7714b79136b7b
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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