Glycine, N-methyl-, hydrochloride (1:1) → HCID 66615086, compound

HRID 717653Notes

Reaction equation

HRID 717653 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]2[S:17][C:16]([C:18]3[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=3)=[CH:15][CH:14]=2)[CH:9]([CH3:11])[CH3:10])=[CH:4][CH:3]=1.Cl.[NH:27]([CH2:29][C:30]([OH:32])=[O:31])[CH3:28].[CH3:33]CN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CC(O)=O.C(Cl)Cl>[CH3:33][O:31][C:30](=[O:32])[CH2:29][N:27]([CH2:22][C:21]1[CH:24]=[CH:25][C:18]([C:16]2[S:17][C:13]([CH2:12][N:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:9]([CH3:11])[CH3:10])=[CH:14][CH:15]=2)=[CH:19][CH:20]=1)[CH3:28]

Participants

8

Reactant 4

HCID 69483Glycine, N-methyl-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 866606114-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde

Product 1

HCID 66615086HCID 66615086, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product of Step B (0.09 g, 0.26 mmol) and sarcosine hydrochloride (0.07 g, 0.5 mmol) in 1,2-dichloroethane (5 ml) was added DIPEA (0.1 ml) and 10 drops of AcOH, followed by NaBH(OAc)3 (0.11 g, 0.51 mmol). The mixture was stirred overnight at room temperature and diluted to 20 ml with CH2Cl2. The organic layer was washed with NaHCO3 solution, H2O and dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.113 g, 100%) as creamy paste. 1H-NMR (CDCl3) 7.47 (d, 2H, J=8.19 Hz); 7.28 (d, 2H, J=8.18 Hz); 7.10 (d, 1H, J=3.62 Hz); 6.88-6.85 (m, 3H); 6.85-6.77 (m, 2H); 4.44 (s, 2H); 4.07-3.98 (m, 1H); 3.69 (s, 3H); 3.24 (s, 2H); 2.37 (s, 3H); 1.21 (d, 6H, J=6.6 Hz).

Workup

  1. washThe organic layer was washed with NaHCO3 solution, H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by FCC (SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-7f64cc14936e47a596efabe683bdcd07
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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