Isopropylamine → HCID 90409016, compound

HRID 589142Notes

Reaction equation

HRID 589142 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)[CH:8]=2)=[C:5]([CH3:28])[O:4][N:3]=1.[CH3:29][CH:30]([NH2:32])[CH3:31].C([BH3-])#N.[Na+]>CO>[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][NH:32][CH:30]([CH3:31])[CH3:29])[CH:8]=2)=[C:5]([CH3:28])[O:4][N:3]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 5003444Sodium cyanoborohydrideHCID 90409434HCID 90409434, compound

Product 1

HCID 90409016HCID 90409016, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
60 °C

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, 0.04 mmol) from Example 137, Step 3 was stirred in methanol (1.0 mL) with 2-propanamine (10 μL, 0.12 mmol), followed by addition of sodium cyanoborohydride (7.5 mg, 0.12 mmol). The mixture was heated at 60° C. overnight, then diluted with methanol. Purification by preparative LCMS (pH 10) afforded the title compound. LCMS calc. for C23H26N5O3 (M+H)+: m/z=420.2. found: 420.1.

Workup

  1. customPurification by preparative LCMS (pH 10)

Sources & evidence

ORD record
ord-35b2907fafa248cb9cc0b492644b69ef
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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