Methanol → HCID 68604241, compound

HRID 709871Notes

Reaction equation

HRID 709871 reaction equation
[NH2:1][C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:15]=2)[N:10]=1)([CH3:8])[C:3](OCC)=[O:4].CO.O1CCCC1.[BH4-].[Na+]>>[NH2:1][C:2]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH:15]=2)[N:10]=1)([CH3:8])[CH2:3][OH:4]

Participants

5

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 68606297HCID 68606297, compound

Product 1

HCID 68604241HCID 68604241, compoundYield 90.3%

Procedure

Ethyl 2-amino-2-(6-heptyloxyquinolin-2-yl)propanoate (7, 5.0 mg, 0.000014 mol) was dissolved in a mixture of methanol (1.0 mL, 0.025 mol) and tetrahydrofuran (1.0 mL, 0.012 mol), followed by sodium tetrahydroborate (1.06 mg, 0.0000279 mol) in small portions at 23° C. The reaction mixture was then allowed to stir for 2 hours. The reaction mixture was quenched with NH4Cl (sat), and solvents were removed under vacuum. The solid residue was then treated with MeOH/DCM, and the crude product was purified via HPLC to give pure product (4 mg, 70%). 1H NMR (CHLOROFORM-d) δ: 8.22 (d, J=8.5 Hz, 1H), 7.97 (d, J=9.3 Hz, 1H), 7.39-7.51 (m, 2H), 7.10 (d, J=2.5 Hz, 1H), 4.14 (br. s., 2H), 4.08 (t, J=6.5 Hz, 2H), 1.81-1.93 (m, 2H), 1.77 (s, 3H), 1.50 (d, J=8.0 Hz, 2H), 1.21-1.44 (m, 6H), 0.81-0.99 (m, 3H). MS (ES, M+1): 317.30.

Workup

  1. customThe reaction mixture was quenched with NH4Cl (sat), and solvents
  2. customwere removed under vacuum
  3. additionThe solid residue was then treated with MeOH/DCM
  4. customthe crude product was purified via HPLC

Sources & evidence

ORD record
ord-698ad06e78a14d6ea1585b0a32003518
Source dataset
uspto-grants-2015_11
Patent number
US09181191B2

Reaction notes

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