Ethylamine → HCID 86298910, compound

HRID 589030Notes

Reaction equation

HRID 589030 reaction equation
CC1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=4[O:19][CH2:20][C:21](O)=[O:22])[N:12]4[C:28](=[O:30])[NH:29][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:31])[O:4]N=1.[CH3:32][CH2:33][N:34](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:65]([NH2:67])[CH3:66]>CN(C=O)C>[CH3:66][C:65]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][CH:13]([C:17]4[CH:27]=[CH:26][CH:25]=[CH:24][C:18]=4[O:19][CH2:20][C:21]([NH:34][CH2:33][CH3:32])=[O:22])[N:12]4[C:28](=[O:30])[NH:29][C:10]([C:11]=34)=[CH:9][CH:8]=2)=[C:5]([CH3:31])[O:4][N:67]=1

Participants

6

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90409785HCID 90409785, compound

Product 1

HCID 86298910HCID 86298910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {2-[7-(3,5-dimethylisoxazol-4-yl)-2-oxo-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl]phenoxy}acetic acid (0.03 g, 0.07 mmol) in DMF (2.0 mL) with DIPEA (0.025 mL, 0.14 mmol) and HATU (0.027 g, 0.071 mmol) was stirred at room temperature for 10 min. and ethylamine (0.0064 g, 0.14 mmol) was added. The reaction mixture was stirred for 1 h and the product was purified without workup by preparative HPLC on a C-18 column eluting with a water:MeCN gradient buffered pH 2 buffered with TFA to give the title compound as an off-white amorphous solid. LCMS calc. for C24H25N4O5 (M+H)+: m/z=449.1. found: 449.2.

Workup

  1. stirringThe reaction mixture was stirred for 1 h
  2. customthe product was purified without workup by preparative HPLC on a C-18 column
  3. washeluting with a water

Sources & evidence

ORD record
ord-ee4c17bf8aac4de3a7076168c759a62e
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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