Sodium triacetoxyborohydride → HCID 59605597, compound

HRID 1946007Notes

Reaction equation

HRID 1946007 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]=O)[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2].[N:30]1([CH:35]2[CH2:38][NH:37][CH2:36]2)[CH2:33][CH:32]([OH:34])[CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH2:18][N:37]4[CH2:38][CH:35]([N:30]5[CH2:33][CH:32]([OH:34])[CH2:31]5)[CH2:36]4)[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 59605518HCID 59605518, compoundHCID 596059872-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 59605597HCID 59605597, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde (0.15 g, 0.38 mmol), [1,3′]biazetidinyl-3-ol (0.098 g, 0.77 mmol) and 4 Å molecular sieves (0.8 g) in DCE (8 mL) was stirred for 4 h at room temperature. Sodium triacetoxyborohydride (0.162 g, 0.77 mmol) was added and the reaction mixture was stirred for 18 h at room temperature. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 20:80) to give 494 as an off-white solid (0.101 g, 53%). LCMS (Method I): RT=2.31 min, [M+H]+ 504.2. 1H NMR (400 MHz, DMSO-d6): δ 8.03-7.98 (m, 1 H); 7.65-7.60 (m, 1 H); 7.28-7.22 (m, 2 H); 5.26 (d, J=6.8 Hz, 1 H); 4.28-4.21 (m, 4 H); 4.19-4.15 (m, 3 H); 3.83 (s, 2 H); 3.79-3.75 (m, 7 H); 3.47-3.35 (m, 2 H); 3.20 (q, J=7.4 Hz, 2 H); 3.02 (t, J=6.8 Hz, 2 H); 2.82 (t, J=6.8 Hz, 3 H); 1.36-1.29 (q, J=7.4 Hz, 3 H)

Workup

  1. stirringthe reaction mixture was stirred for 18 h at room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash chromatography (Si—PPC, MeOH:DCM, gradient 0:100 to 20:80)

Sources & evidence

ORD record
ord-8056dec27e22498492cdd48e38b0a555
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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