Borane → HCID 68182920, compound

HRID 1615565Notes

Reaction equation

HRID 1615565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([C:15](O)=[O:16])[NH:13][C:12](=[O:18])[C:11]3[S:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:21][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8].B.C1COCC1>>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C@H:14]([CH2:15][OH:16])[NH:13][C:12](=[O:18])[C:11]3[S:19][C:20]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[CH:21][C:10]2=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 68183276HCID 68183276, compound

Product 1

HCID 68182920HCID 68182920, compoundYield 26.6%

Procedure

A flask was charged with rel-(4R,5R)-4-(3,4-dichlorophenyl)-2-(morpholin-4-yl)-7-oxo-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-5-carboxylic acid (0.100 g, 0.234 mmol) and borane in THF (1M, 2.34 mmol, 2.34 mmol) was added. The mixture was stirred at rt for 2 hours. The reaction mixture was quenched by addition of methanol and then purified using preparative HPLC to afford the product as a white solid (25.7 mg, 26.3%). LCMS (AA) ES+: 413.4, 415.4, 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=8.3 Hz, 1H), 7.33 (d, J=2.0 Hz, 1H), 7.08 (dd, J=8.2, 2.1 Hz, 1H), 5.82 (s, 1H), 5.47 (s, 1H), 3.99 (d, J=8.9 Hz, 2H), 3.83-3.76 (m, 4H), 3.18-3.11 (m, 4H).

Workup

  1. additionwas added
  2. customThe reaction mixture was quenched by addition of methanol
  3. custompurified

Sources & evidence

ORD record
ord-65852f6ff8dd49618c802e690950eec3
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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