Sodium triacetoxyborohydride → HCID 59605807, compound

HRID 1923113Notes

Reaction equation

HRID 1923113 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].[O:30]1[C:35]2([CH2:40][CH2:39][NH:38][CH2:37][CH2:36]2)[CH2:34][NH:33][C:32](=[O:41])[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:38]4[CH2:37][CH2:36][C:35]5([O:30][CH2:31][C:32](=[O:41])[NH:33][CH2:34]5)[CH2:40][CH2:39]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 130594341-Oxa-4,9-diazaspiro(5.5)undecan-3-oneHCID 596059872-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 59605807HCID 59605807, compoundYield 83%

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 (100 mg, 0.26 mmol), 1-oxa-4,9-diazaspiro[5.5]undecan-3-one (61 mg, 0.36 mmol) and molecular sieves (4 Å, powdered, 255 mg) in DCE (5 mL) was stirred at ambient temperature for 1 h. Sodium triacetoxyborohydride (81 mg, 0.38 mmol) was added and the mixture stirred for 17 h, then loaded onto an Isolute® SCX-2 cartridge (10 g). The cartridge was then washed with methanol and the desired product was subsequently eluted using 2 M NH3 in MeOH. The product was collected and concentrated in vacuo. The resultant residue was purified by flash chromatography (Si—PPC, EtOAc: MeOH; gradient from 100:0 to 70:30) to afford 394 as a cream solid (116 mg, 83%). LCMS (Method G): RT=5.76 min, M+H'=546. 1H NMR (CDCl3, 400 MHz) δ 8.01 (m, 1 H); 7.77 (m, 1 H); 7.32-7.24 (m, 2 H); 5.93 (bs, 1 H); 4.35 (m, 4 H); 4.18 (s, 2 H); 3.90-3.84 (m, 7 H); 3.82 (bs, 2H); 3.37 (q, J=7.5 Hz, 2 H); 3.27 (m, 2 H); 2.72 (m, 2 H); 2.59 (m, 2 H); 2.05-1.93 (m, 2H); 1.68 (m, 2 H) and 1.46 (t, J=7.5 Hz, 3 H)

Workup

  1. stirringthe mixture stirred for 17 h
  2. washThe cartridge was then washed with methanol
  3. washthe desired product was subsequently eluted
  4. customThe product was collected
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by flash chromatography (Si—PPC, EtOAc: MeOH; gradient from 100:0 to 70:30)

Sources & evidence

ORD record
ord-ddc5b229df454818867d9a47484d254a
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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