Sodium borohydride → HCID 86299248, compound

HRID 589143Notes

Reaction equation

HRID 589143 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][C@H:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[N:12]4[C:23](=[O:25])[NH:24][C:10]([C:11]=34)=[C:9]([CH:26]=[O:27])[CH:8]=2)=[C:5]([CH3:28])[O:4][N:3]=1.[BH4-].[Na+]>C(O)C>[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[N:12]4[C:23](=[O:25])[NH:24][C:10]([C:11]=34)=[C:9]([CH2:26][OH:27])[CH:8]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90409434HCID 90409434, compound

Product 1

HCID 86299248HCID 86299248, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-(3,5-Dimethylisoxazol-4-yl)-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazine-9-carbaldehyde (15 mg, 0.040 mmol) from Example 137, Step 3 was stirred in ethanol (0.58 mL), followed by addition of sodium tetrahydroborate (2.3 mg, 0.060 mmol). The mixture was stirred at room temperature for 1 h. Purification by preparative LCMS (pH 10) afforded the title compound. LCMS calc. for C20H19N4O4 (M+H)+: m/z=379.1. found: 379.2.

Workup

  1. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-737fcb4b98b44694971fbd5c15857f11
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

Loading…