Acetic Acid → HCID 11519456, compound

HRID 2219902Notes

Reaction equation

HRID 2219902 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@H:9]([N:13]1[CH:17]=[C:16]([CH2:18][C@@H:19]([NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:20]([NH2:22])=[O:21])[N:15]=[N:14]1)[CH2:8][CH2:7][CH2:6]2)=O.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[CH3:33][C:30]1[CH:29]=[CH:28][C:27]([S:24]([NH:23][C@H:19]([CH2:18][C:16]2[N:15]=[N:14][N:13]([C@H:9]3[C:10]4[C:5](=[CH:4][C:3]([CH2:1][N:34]5[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]5)=[CH:12][CH:11]=4)[CH2:6][CH2:7][CH2:8]3)[CH:17]=2)[C:20]([NH2:22])=[O:21])(=[O:26])=[O:25])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 59771821HCID 59771821, compound

Product 1

HCID 11519456HCID 11519456, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of (R)-3-(1-((R)-6-formyl-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-1,2,3-triazol-4-yl)-2-(4-methylbenzenesulfonamido)propanamide (0.21 g, 0.45 mmol) and piperidine (0.20 g, 2.2 mmol) in 5 mL 1,2-dichloroethane was heated to 60° C. for 30 min. The reaction mixture was cooled and treated with NaBH(OAc)3 and a drop of HOAc. The resulting mixture was heated to 80° C. for 16 h. The reaction mixture was cooled, quenched with H2O, and extracted with CHCl3 (3×). The combined extracts were dried over MgSO4, concentrated and purified by SiO2 (5% MeOH/CH2Cl2) to give a white solid. MS (m/z): 537.4 (m+H).

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe resulting mixture was heated to 80° C. for 16 h
  3. temperatureThe reaction mixture was cooled
  4. customquenched with H2O
  5. extractionextracted with CHCl3 (3×)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. concentrationconcentrated
  8. custompurified by SiO2 (5% MeOH/CH2Cl2)
  9. customto give a white solid

Sources & evidence

ORD record
ord-17d8da2960a34060b10b0308853b7529
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

Loading…