Hydrochloric Acid → HCID 67257706, compound

HRID 1509191Notes

Reaction equation

HRID 1509191 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[CH2:8][O:7][C:6]2[N:11]=[C:12]([C:21]3[CH:26]=[CH:25][C:24]([C:27]4([NH:31]C(=O)OC(C)(C)C)[CH2:30][CH2:29][CH2:28]4)=[CH:23][CH:22]=3)[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:14][C:5]1=2.Cl>ClCCl>[NH2:31][C:27]1([C:24]2[CH:25]=[CH:26][C:21]([C:12]3[C:13]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:14][C:5]4[N:4]([CH2:3][CH2:2][OH:1])[C:9](=[O:10])[CH2:8][O:7][C:6]=4[N:11]=3)=[CH:22][CH:23]=2)[CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86683597HCID 86683597, compound

Product 1

HCID 67257706HCID 67257706, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a round bottomed flask containing tert-butyl 1-(4-(1-(2-hydroxyethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (25 mg, 0.048 mmol) was added dichloromethane (2.5 ml) followed with hydrochloric acid (2.5 ml, 2M in diethyl ether). The resulting solution was stirred for 16 h. The precipitate was filtered and washed with ether (2×10 ml) and dried to afford the product (15.5 mg). 1H NMR (500 MHz, CH3OD) 7.78 (s, 1H), 7.42 (d, 2H), 7.38 (d, 2H), 7.30 (m, 3H), 7.22 (m, 2H), 4.96 (s, 2H), 4.16 (t, 2H), 3.86 (t, 2H), 2.73-2.79 (m, 2H), 2.54-2.60 (m, 2H), 2.21-2.26 (m, 1H), 1.94-1.99 (m, 1H). LCMS (Method D): RT=1.99 min, M+H+=416.2.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ether (2×10 ml)
  3. customdried

Sources & evidence

ORD record
ord-8eba0ece145045aeba0502f280f61069
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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