Hydrochloric Acid → HCID 90409439, compound

HRID 589074Notes

Reaction equation

HRID 589074 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[C:16]3[O:15][CH2:14][C:13]([CH2:23][NH:24]C(=O)C)([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=4)[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:3]=1.Cl>O1CCCC1.O>[NH2:24][CH2:23][C:13]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:12]2[C:28](=[O:30])[NH:29][C:10]3=[CH:9][CH:8]=[C:7]([C:6]4[C:2]([CH3:1])=[N:3][O:4][C:5]=4[CH3:31])[C:16](=[C:11]23)[O:15][CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86299125HCID 86299125, compound

Product 1

HCID 90409439HCID 90409439, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

N-{[7-(3,5-Dimethylisoxazol-4-yl)-2-oxo-4-pyridin-2-yl-1,2,4,5-tetrahydroimidazo[1,5,4-de][1,4]benzoxazin-4-yl]methyl}acetamide (10 mg, 0.02 mmol) was dissolved in tetrahydrofuran (1 mL) and concentrated hydrochloric acid (200 μL, 6 mmol) in water (800 μL). The reaction was heated to 100° C. for 4 h and was then purified without workup by prep HPLC on a C-18 column eluting a water:acetonitrile gradient buffered at pH 2 with TFA to give 4-(aminomethyl)-7-(3,5-dimethylisoxazol-4-yl)-4-pyridin-2-yl-4,5-dihydroimidazo[1,5,4-de][1,4]benzoxazin-2(1H)-one as off white solid (0.0045 g, 40%). LCMS calculated for C20H20N5O3 (M+H)+: m/z=378.1. found: 378.1. 1H NMR (400 MHz, DMSO-d6) δ 11.40 (s, 1H), 8.68-8.58 (m, 1H), 8.20 (bs, 2H), 7.84 (td, J=7.8, 1.8 Hz, 1H), 7.48-7.37 (m, 1H), 7.16 (d, J=8.0 Hz, 1H), 6.91 (d, J=8.0 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 4.73 (d, 1H), 4.41 (d, 1H), 4.12-3.97 (m, 1H), 3.75-3.58 (m, 1H), 2.18 (s, 3H), 2.00 (s, 3H).

Workup

  1. customwas then purified without workup by prep HPLC on a C-18 column
  2. washeluting a water

Sources & evidence

ORD record
ord-ca8df3fbdd024bd8abb3aa1a1742ea45
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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