Triethylamine → HCID 86299223, compound

HRID 589138Notes

Reaction equation

HRID 589138 reaction equation
C(N(CC)CC)C.[NH:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1.Cl[C:15]1[N:23]2[CH:24]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH2:25][O:26][C:21]3=[C:22]2[C:17](=[C:18]([F:40])[CH:19]=[C:20]3[C:33]2[C:34]([CH3:39])=[N:35][O:36][C:37]=2[CH3:38])[N:16]=1>CN1CCCC1=O.CO>[CH3:39][C:34]1[C:33]([C:20]2[C:21]3[O:26][CH2:25][CH:24]([C:27]4[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=4)[N:23]4[C:15]([N:8]5[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]5)=[N:16][C:17]([C:22]=34)=[C:18]([F:40])[CH:19]=2)=[C:37]([CH3:38])[O:36][N:35]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 982104-HydroxypyrrolidineHCID 90409257HCID 90409257, compound

Product 1

HCID 86299223HCID 86299223, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

Triethylamine (16 μL, 0.12 mmol) and 3-pyrrolidinol (0.2 mL, 3 mmol) were added to 2-chloro-7-(3,5-dimethylisoxazol-4-yl)-9-fluoro-4-pyridin-3-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazine (15 mg, 0.040 mmol) in N-methylpyrrolidinone (0.41 mL) and the mixture was heated in a microwave at 150° C. for 20 min. The mixture was diluted with methanol and purified by preparative LCMS using pH 10 buffer to afford the title compound (2.4 mg, 14%). LCMS calc. for C23H23FN5O3 (M+H)+: m/z=436.2. found: 436.1.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-c146f670a60f45eda2e6b634fdbfe984
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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