Sodium triacetoxyborohydride → HCID 178503378, compound

HRID 1984622Notes

Reaction equation

HRID 1984622 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=3)=[N:9][C:7]=2[N:8]=1.Cl.[NH:28]1[CH2:33][CH2:32][CH:31]([C:34]2[N:38]=[C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)[NH:36][N:35]=2)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O.CN(C=O)C>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([C:19]3[CH:26]=[CH:25][C:22]([CH2:23][N:28]4[CH2:33][CH2:32][CH:31]([C:34]5[NH:38][C:37]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=6)=[N:36][N:35]=5)[CH2:30][CH2:29]4)=[CH:21][CH:20]=3)=[N:9][C:7]=2[N:8]=1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 57713942HCID 57713942, compoundHCID 178477979HCID 178477979, compound

Product 1

HCID 178503378HCID 178503378, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-[2-(methylthio)-6-phenylpyrido[2,3-d]pyrimidin-7-yl]benzaldehyde (1-4) (0.200 g, 0.56 mmol), 2-(3-piperidin-4-yl-1H-1,2,4-triazol-5-yl)pyridine HCl salt (A [see synthesis below]; 0.193 g, 0.727 mmol), and TEA (0.074 g, 0.727 mmol) were stirred in 5% AcOH in DMF for 0.5 hr. Sodium triacetoxyborohydride (0.178 g, 0.0.839 mmol) was then added and the reaction was stirred for 3 hr. The reaction was quenched with 3N NaOH and extracted 3×w/CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silicon gel chromatography (6% MeOH in CH2Cl2) to give the titled compound. 1H-NMR (500 MHz, d6 DMSO) δ 9.50 (s, 1H), 8.64-8.72 (m, 2H), 8.58 (s, 1H), 7.88-8.07 (m, 3H), 7.28-7.56 (m, 9H), 3.52 (s, 2H), 2.84 (m, 2H), 2.66 (s, 3H), 2.11 (m, 3H), 1.96 (m, 2H), 1.78 (m, 2H). LRMS m/z (M+H) calcd: 571.7, found: 571.2.

Workup

  1. customA [see synthesis below]
  2. customThe reaction was quenched with 3N NaOH
  3. extractionextracted 3×w/CH2Cl2
  4. dry with materialThe combined organics were dried (anhd. Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silicon gel chromatography (6% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e7a73a069ad14919861dfe667dff8bf7
Source dataset
uspto-grants-2009_06
Patent number
US07544677B2

Reaction notes

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