Lithium borohydride → HCID 70976181, compound

HRID 535544Notes

Reaction equation

HRID 535544 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([NH:17][C:18](=[O:27])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:7]=1)C.[Li+].[BH4-]>C1COCC1>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C:18]([NH:17][N:8]2[N:7]=[C:6]([CH2:5][CH2:4][OH:3])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:16])=[O:27])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 123428840HCID 123428840, compound

Product 1

HCID 70976181HCID 70976181, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 0° C. solution of the product from Example 116 (365 mg, 0.938 mmol) in THF (10 mL) was added LiBH4 in THF (2M, 0.69 mL, 1.4 mmol). The mixture was stirred for 6 hours, quenched with water (10 mL), extracted with EtOAc (4×20 mL), dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (0-100% of 1/10 MeOH/EtOAc in hexanes) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.56 (s, 1H), 8.31 (dd, J=7.9, 1.4, 1H), 8.08 (d, J=8.1, 1H), 8.04-7.94 (m, 1H), 7.94-7.85 (m, 1H), 7.43-7.35 (m, 4H), 4.74 (t, J=5.4, 1H), 3.81-3.71 (m, 2H), 3.68 (s, 2H), 3.08 (t, J=6.7, 2H); MS (ESI+) M/Z 358 (M+H)+.

Workup

  1. customquenched with water (10 mL)
  2. extractionextracted with EtOAc (4×20 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (0-100% of 1/10 MeOH/EtOAc in hexanes)

Sources & evidence

ORD record
ord-ad4e5c71052c45d1a477834d7d01046a
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

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