Sarcosine → HCID 46941016, compound

HRID 2410605Notes

Reaction equation

HRID 2410605 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)=[C:21]([CH3:27])[CH:20]=3)[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])=[C:21]([CH3:27])[CH:20]=3)[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 86661517HCID 86661517, compound

Product 1

HCID 46941016HCID 46941016, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (35 mg, 0.55 mmol) was added into a solution of 4-(5-(2-(methoxymethyl)-2′-methylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl)-2-methylbenzaldehyde (194 mg, 0.49 mmol) and 2-(methylamino)acetic acid (86 mg, 0.97 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 white solid. 1H NMR (DMSO-d6, 400 MHz) δ 8.47-8.31 (1H, m), 8.15-8.09 (1H, m), 8.06-7.99 (2H, m), 7.69 (1H, d, J=7.9 Hz), 7.33-7.20 (4H, m), 7.11 (1H, d, J=7.4 Hz), 4.33 (2H, s), 4.21 (2H, m), 3.67 (2H, s), 3.30 (3H, s), 2.78 (3H, s), 2.54 (3H, s), 2.07 (3H, s). LC/MS (Method A): 472 (M+H)+. HPLC (Method F) Rt 3.19 min (Purity: 98.5%).

Workup

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

Sources & evidence

ORD record
ord-00b2d4c676804924afa21b02fa6b13ef
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

Loading…