Acetic Acid → HCID 59605461, compound

HRID 1945639Notes

Reaction equation

HRID 1945639 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH:13]=O)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1.[N:21]1([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(OC)(OC)OC.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:12][CH2:13][N:24]3[CH2:23][CH2:22][N:21]([C:27]([CH3:32])([CH3:31])[C:28]([NH2:30])=[O:29])[CH2:26][CH2:25]3)[N:8]2[CH3:11])=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[N:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 5049666Sodium triacetoxyborohydrideHCID 217488412-Methyl-2-(piperazin-1-yl)propanamideHCID 59605819(2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde

Product 1

HCID 59605461HCID 59605461, compoundYield 42.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (2-chloro-9-methyl-6-morpholin-4-yl-9H-purin-8-yl)acetaldehyde (110 mg, 0.37 mmol) in DCE (10 mL) was added 2-piperazin-1-ylisobutyramide (90 mg, 0.53 mmol), trimethyl orthoformate (0.20 mL, 1.86 mmol) and acetic acid (0.02 mL, 0.37 mmol). The reaction mixture was stirred at room temperature for 3 h, sodium triacetoxyborohydride (118 mg, 0.56 mmol) was added and the resulting mixture stirred for a further 2 days. The reaction mixture was loaded onto an Isolute® SCX-2 cartridge, the cartridge was washed with MeOH then the desired product eluted with 2 M NH3 in MeOH. The resulting residue was purified by column chromatography (Si—PCC, 0-20% MeOH in EtOAc) to give the title compound as a pale yellow solid (71 mg, 42%). LCMS (Method H): RT=2.40 min, [M+H]+ 451.5

Workup

  1. stirringthe resulting mixture stirred for a further 2 days
  2. washthe cartridge was washed with MeOH
  3. washthe desired product eluted with 2 M NH3 in MeOH
  4. customThe resulting residue was purified by column chromatography (Si—PCC, 0-20% MeOH in EtOAc)

Sources & evidence

ORD record
ord-594f2e3b34ee404ebd7a205bbfee7ecb
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

Loading…