Lithium borohydride → HCID 70689990, compound

HRID 528980Notes

Reaction equation

HRID 528980 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:8]=[C:7]([C:16](OCC)=[O:17])[C:6]=1[C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:42])[NH:28][S:29]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)(=[O:31])=[O:30])=[CH:23][C:22]=1[C:43]([N:45]1[CH2:54][CH2:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46]1)=[O:44])[CH2:2][CH2:3][CH3:4].[BH4-].[Li+]>C1COCC1>[CH2:1]([C:5]1[N:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:8]=[C:7]([CH2:16][OH:17])[C:6]=1[C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH:28][S:29]([C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)(=[O:30])=[O:31])=[O:42])=[CH:23][C:22]=1[C:43]([N:45]1[CH2:54][CH2:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH2:46]1)=[O:44])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 70694200HCID 70694200, compound

Product 1

HCID 70689990HCID 70689990, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 25 mL round bottom flask was charged with ethyl 5-butyl-4-(4-(naphthalen-2-ylsulfonylcarbamoyl)-2-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-1-phenyl-1H-pyrazole-3-carboxylate (Example 223, 23 mg, 0.031 mmol). THF (1.0 mL) and then 2M lithium borohydride solution in THF (0.078 mL, 0.16 mmol) were added. The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with sat. aq. sodium bicarbonate solution and extracted with EtOAc. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product. The residue was purified by preparative HPLC to give the title compound (7.3 mg, 34%). 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.65 (s, 1H), 8.12-7.91 (m, 6H), 7.63-7.57 (m, 2H), 7.50-6.99 (m, 9.5H), 6.91-6.89 (m, 0.5H), 4.65-4.32 (m, 4H), 3.44-3.15 (m, 2H), 2.88-2.49 (m, 4H), 1.39-0.86 (m, 4H), 0.55-0.49 (m, 3H); MS(ESI+) m/z 699.2 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with sat. aq. sodium bicarbonate solution
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the crude product
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f9e3112c42b2434ba04b243f87dc12d2
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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