Acetonitrile → HCID 59993249, compound

HRID 238248Notes

Reaction equation

HRID 238248 reaction equation
C([O:3][C:4]([C:6]1[C:7]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[N:8][C:9]([CH:12]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH2:16][CH2:15]2)[CH3:13])=[N:10][CH:11]=1)=O)C.[BH4-].[Na+].CC#N>C(O)C>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:17]2[CH2:16][CH2:15][N:14]([CH:12]([C:9]3[N:8]=[C:7]([N:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[C:6]([CH2:4][OH:3])=[CH:11][N:10]=3)[CH3:13])[CH2:19][CH2:18]2)(=[O:21])=[O:22])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 4311764Sodium borohydrideHCID 59993216HCID 59993216, compound

Product 1

HCID 59993249HCID 59993249, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{1-[4-(4-methoxy-benzenesulfonyl)-piperazin-1-yl]-ethyl}-4-piperidin-1-yl-pyrimidine-5-carboxylic acid ethyl ester (104 mg, 0.2 mmol) in ethanol (1 mL) was added sodium borohydride (38 mg, 1.0 mmol) and the reaction mixture was heated to reflux for 1 day. The reaction was then partition between dichloromethane and saturated sodium bicarbonate solution. The organic layer was concentrated in vacuo and then the residue was dissolved in DMSO (1 mL) and purified by LC-MS to yield the product. 1H NMR (400 MHz, CDCl3) δ 8.26 (s, 1H), 7.65 (d, J=8.8 Hz, 2H), 7.03 (d, J=8.8 Hz, 2H), 4.62 (s, 2H), 4.53 (q, J=6.6 Hz, 1H), 3.93 (m, 7H), 3.25 (m, 8H), 1.77 (m, 6H), 1.67 (d, J=6.8 Hz, 3H); HPLC ret. time 2.49 min, 10-99% CH3CN, 5 min run; ESI-MS m/z 476.1 (M+1)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 day
  3. customThe reaction was then partition between dichloromethane and saturated sodium bicarbonate solution
  4. concentrationThe organic layer was concentrated in vacuo
  5. dissolutionthe residue was dissolved in DMSO (1 mL)
  6. custompurified by LC-MS
  7. customto yield the product

Sources & evidence

ORD record
ord-dd52a7afaf4c48edb79ddce587a25fd3
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

Loading…