Triethylamine → HCID 58043129, compound

HRID 1035254Notes

Reaction equation

HRID 1035254 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:19][CH:18]([O:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([CH3:29])[CH:22]=4)[CH2:17]3)=[O:15])=[N:11][N:10]=2)=[CH:5][CH:4]=1.Cl.[CH3:31][C:32]1([CH2:38][OH:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:39][CH2:38][C:32]1([CH3:31])[CH2:37][CH2:36][N:35]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH:18]3[CH2:19][N:16]([C:14]([C:12]4[O:13][C:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)=[N:10][N:11]=4)=[O:15])[CH2:17]3)=[CH:22][C:23]=2[CH3:29])[CH2:34][CH2:33]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 580431564-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methylbenzaldehydeHCID 66653509(4-Methylpiperidin-4-yl)methanol--hydrogen chloride (1/1)

Product 1

HCID 58043129HCID 58043129, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

73C (0.12 g, 0.31 mmol) and (4-methylpiperidin-4-yl)methanol hydrochloride (0.051 g, 0.31 mmol) were mixed with DCM (3 ml). Triethylamine (0.085 ml, 0.61 mmol) and then sodium triacetoxyborohydride (0.129 g, 0.61 mmol) were added. The mixture was stirred at RT overnight and then diluted with DCM (10 ml). The mixture was washed with aqueous NaHCO3 (sat. 4 ml) and then the organic solution was filtered through a phase separator. The solvent was removed by evaporation and the residue was purified by silica gel chromatography eluting the product with 1-3% methanol in DCM where the methanol contained ammonia (2 M). The product was triturated from DCM/diethylether. There was obtained 102 mg (66%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ 0.95 (s, 3H), 1.32 (m, 2H), 1.53 (m, 2H), 2.30 (m, 2H), 2.34 (s, 3H), 2.53 (m, 2H), 3.38 (m, 2H), 3.42 (s, 2H), 3.89 (s, 3H), 4.32 (m, 1H), 4.63 (m, 1H), 4.72 (m, 1H), 5.04 (m, 2H), 5.10 (m, 1H), 6.55 (d, 2H), 6.59 (s, 1H), 7.03 (d, 2H), 7.19 (m, 2H), 8.10 (d, 2H), MS (APCI+) m/z 507 [M+H]+, LC purity: 98%.

Workup

  1. washThe mixture was washed with aqueous NaHCO3 (sat. 4 ml)
  2. filtrationthe organic solution was filtered through a phase separator
  3. customThe solvent was removed by evaporation
  4. customthe residue was purified by silica gel chromatography
  5. washeluting the product with 1-3% methanol in DCM where the methanol
  6. customThe product was triturated from DCM/diethylether

Sources & evidence

ORD record
ord-74d44dc6702b4c5a9fd7859a3cbaf990
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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