2,6-Dichlorobenzaldehyde → N5-[1-(2,6-Dichloro-benzyl)-pyrrolidin-2-ylmethyl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

HRID 1181292Notes

Reaction equation

HRID 1181292 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:22]=[C:9]2[N:10]=[C:11]([NH:15][CH2:16][CH:17]3[CH2:21][CH2:20][CH2:19][NH:18]3)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:25]=1[CH2:26][N:18]1[CH2:19][CH2:20][CH2:21][CH:17]1[CH2:16][NH:15][C:11]1[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=[C:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[N:22]=[C:9]2[N:10]=1

Participants

6

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 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 11351611N5-[1-(2,6-Dichloro-benzyl)-pyrrolidin-2-ylmethyl]-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazine-5,7-diamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

2-Furan-2-yl-N5-pyrrolidin-2-ylmethyl-[1,2,4]-triazolo[1,5-a][1,3,5]triazine-5,7-diamine (0.15 mmol) was dissolved in 4 mL of CH2Cl2 along with 2 eq. of 2,6-dichlorobenzaldehyde and 25 mL of glacial acetic acid. The reaction mixture was stirred at room temperature for 30 minutes and sodium triacetoxyborohydride (4 eq.) was added in a single portion. The resulting reaction mixture was then stirred at room temperature for 18 hours. It was then concentrated under a stream of N2 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), 6.95-7.0 (m, 3H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H), 2.2-3.2 (m, 8H). MS: m/z: 460[M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas then stirred at room temperature for 18 hours
  3. concentrationIt was then concentrated under a stream of N2
  4. custompurified by preparative HPLC
  5. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-58d30cb8355f4368a681f294a3f19836
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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