Sodium triacetoxyborohydride → HCID 66641284, compound

HRID 1094236Notes

Reaction equation

HRID 1094236 reaction equation
C(O[BH-](O[C:11](=O)[CH3:12])OC(=O)C)(=O)C.[Na+].[NH2:15][CH:16]([CH2:24][NH:25][C:26]1[C:31]([CH2:32][CH3:33])=[C:30]([N:34]2[CH2:39][CH2:38][CH:37]([C:40]3[CH:49]=[CH:48][C:47]4[CH2:46][CH2:45][CH2:44][NH:43][C:42]=4[N:41]=3)[CH2:36][CH2:35]2)[N:29]=[CH:28][N:27]=1)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>O1CCCC1>[CH2:31]([CH:32]([CH2:11][CH3:12])[CH2:33][NH:15][CH:16]([CH2:24][NH:25][C:26]1[C:31]([CH2:32][CH3:33])=[C:30]([N:34]2[CH2:35][CH2:36][CH:37]([C:40]3[CH:49]=[CH:48][C:47]4[CH2:46][CH2:45][CH2:44][NH:43][C:42]=4[N:41]=3)[CH2:38][CH2:39]2)[N:29]=[CH:28][N:27]=1)[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH3:30]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 66641143Tert-butyl 2-amino-3-{5-ethyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate

Product 1

HCID 66641284HCID 66641284, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

75 mg (0.35 mmoles) of sodium triacetoxyborohydride in 6 ml of tetrahydrofuran is left under stirring for 10 minutes at TA. Then a mixture of 100 mg (0.208 mmoles) of tert-butyl 2-amino-3-{5-ethyl-6-[4-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-piperidin-1-yl]-pyrimidin-4-ylamino}-propionate and 0.228 mmoles of 2-ethyl-butylaldehyde in solution in 3 ml of tetrahydrofuran is added. The reaction mixture is stirred at ambient temperature for 4 hours 30 minutes. Then it is extracted with ethyl acetate after washing with a saturated solution of sodium bicarbonate. The organic phase obtained is dried over magnesium sulphate before being concentrated to dryness under reduced pressure (2 kPa). The residue is then chromatographed on silica gel with the following eluent: ethyl acetate-dichloromethane/methanol (80/20) 50-50. A mass my of expected product is obtained.

Workup

  1. additionis added
  2. stirringThe reaction mixture is stirred at ambient temperature for 4 hours 30 minutes
  3. extractionThen it is extracted with ethyl acetate
  4. washafter washing with a saturated solution of sodium bicarbonate
  5. customThe organic phase obtained
  6. dry with materialis dried over magnesium sulphate
  7. concentrationbefore being concentrated to dryness under reduced pressure (2 kPa)
  8. customThe residue is then chromatographed on silica gel with the following eluent

Sources & evidence

ORD record
ord-5ed2722fb0264b109b25d54c20564ed1
Source dataset
uspto-grants-2012_03
Patent number
US08133896B2

Reaction notes

Loading…