Acetic Acid → HCID 21103104, compound

HRID 1354806Notes

Reaction equation

HRID 1354806 reaction equation
[C:1]1([C:7]2[C:8]([C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:25]1[CH2:30][CH2:29][CH:28]([N:31]2[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=3[NH:33][C:32]2=[O:40])[CH2:27][CH2:26]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CN(C=O)C>[C:1]1([C:7]2[C:8]([C:17]3[CH:18]=[CH:19][C:20]([CH2:21][N:25]4[CH2:26][CH2:27][CH:28]([N:31]5[C:35]6[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=6[NH:33][C:32]5=[O:40])[CH2:29][CH2:30]4)=[CH:23][CH:24]=3)=[N:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][N:11]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 21103206HCID 21103206, compound

Product 1

HCID 21103104HCID 21103104, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(3-phenyl-1,8-naphthyridin-2-yl)benzaldehyde (9-3) (135 mg, 0.44 mmole) in dry DMF (2 mL) was added 1-piperidin-4-yl-1,3-dihydro-2H-benzimidazol-2-one (123 mg, 0.57 mmole) and HOAc (0.13 mL, 2.18 mmole) at RT. After 30 min NaBH(OAc)3 (120 mg, 0.57 mmole) was added. After 4 hr the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Flash column (gradient, 0–10% MeOH/CH2Cl2) gave the title compound as a cream colored solid (9-4): 1H-NMR (500 MHz, CDCl3) δ 9.15 (dd, J=1.71, 2.44 Hz, 1 H), 8.56 (bs, 1 H), 8.24 (m, 1 H), 8.19 (s, 1 H), 7.53 (m, 2 H), 7.30 (m, 7 H), 7.06 (m, 3H), 4.36 (m, 1 H), 3.56 (s, 2 H), 3.01 (d, J=11.47 Hz, 2 H), 2.44 (m, 2 H), 2.17 (m, 2H), 1.79 (d, J=11.72 Hz, 2 H); HRMS, calc'd for C33H29N5O (M+1), 512.2445; found 512.2478.

Workup

  1. concentrationAfter 4 hr the mixture was concentrated
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6def5a897d5545109ba09484c078f3f0
Source dataset
uspto-grants-2007_05
Patent number
US07223738B2

Reaction notes

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