2-Chlorobenzaldehyde → HCID 11270218, compound

HRID 1181294Notes

Reaction equation

HRID 1181294 reaction equation
[N:1]1([C:8]2[N:13]=[C:12]([NH2:14])[N:11]3[N:15]=[C:16]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:10]3[N:9]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][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]=[CH:28][C:25]=1[CH2:26][N:4]1[CH2:5][CH2:6][CH2:7][N:1]([C:8]2[N:13]=[C:12]([NH2:14])[N:11]3[N:15]=[C:16]([C:18]4[O:19][CH:20]=[CH:21][CH:22]=4)[N:17]=[C:10]3[N:9]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69431799HCID 69431799, compound

Product 1

HCID 11270218HCID 11270218, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

5-[1,4]Diazepan-1-yl-2-furan-2-yl-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-ylamine (0.15 mmol) was dissolved in 4 mL of CH2Cl2 along with 2 eq. of 2-chloro-benzaldehyde 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 (PMSO-d6) δ 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 6.9-7.2 (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: 426 [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-140ab34a75604c7cab4bd02100d55373
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

Loading…