Sarcosine → HCID 46940830, compound

HRID 2410600Notes

Reaction equation

HRID 2410600 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH3:5][O:6][CH2:7][C:8]1[CH:13]=[C:12]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][C:20]=3[CH3:27])[N:15]=2)[CH:11]=[CH:10][C:9]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34].CN[CH2:37][C:38]([OH:40])=[O:39].C(Cl)Cl>CO.C(O)(=O)C>[CH3:5][O:6][CH2:7][C:8]1[CH:13]=[C:12]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:26]=[CH:25][C:22]([CH2:23][N:2]([CH3:1])[CH2:37][C:38]([OH:40])=[O:39])=[CH:21][C:20]=3[CH3:27])[N:15]=2)[CH:11]=[CH:10][C:9]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]

Participants

7

Reactant 4

HCID 1088SarcosineHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 86661516HCID 86661516, compound

Product 1

HCID 46940830HCID 46940830, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (29.7 mg; 0.47 mmol) was added into a solution of 4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)-3-methylbenzaldehyde (185 mg, 0.43 mmol) and 2-(methylamino)acetic acid (65 mg, 0.87 mmol) in a mixture of methanol (3 mL), DCM (3 mL) and acetic acid (75 μl). The mixture was stirred at room temperature overnight and the solvent was then removed in vacuo. The residue was purified by preparative HPLC to give the title compound as a pale yellow gum. 1H NMR (DMSO-d6, 400 MHz) δ 8.37-8.32 (1H, m), 8.20 (1H, dd, J=7.8, 1.9 Hz), 8.06 (1H, d, J=7.7 Hz), 7.47-7.37 (5H, m), 7.38-7.29 (1H, m), 7.18 (1H, d, J=7.3 Hz), 4.23 (2H, m), 3.78 (2H, s), 3.28 (3H, s), 3.25 (2H, s), 2.67 (3H, s), 2.34 (3H, s), 2.07 (3H, s). LC/MS (Method A): 472 (M+H)+. HPLC (Method F) Rt 3.19 min (Purity: 99.2%).

Workup

  1. customthe solvent was then removed in vacuo
  2. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-a1d5f31e907a49f5aa9f849bb72d4281
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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