HCID 86683571, compound → 1-(6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethanone

HRID 1509143Notes

Reaction equation

HRID 1509143 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][O:7][C:6]2[N:10]=[C:11]([C:20]3[CH:25]=[CH:24][C:23]([C:26]4([NH:30]C(=O)OC(C)(C)C)[CH2:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:13][C:5]1=2)(=[O:3])[CH3:2]>Cl.CCOCC>[NH2:30][C:26]1([C:23]2[CH:22]=[CH:21][C:20]([C:11]3[C:12]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)=[CH:13][C:5]4[N:4]([C:1](=[O:3])[CH3:2])[CH2:9][CH2:8][O:7][C:6]=4[N:10]=3)=[CH:25][CH:24]=2)[CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 86683571HCID 86683571, compound

Product 1

HCID 532620521-(6-(4-(1-aminocyclobutyl)phenyl)-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)ethanoneYield 131.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Tert-butyl (1-(4-(1-acetyl-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (20 mg, 0.04 mmol) was dissolved in 2M HCl in Et2O (1 ml). The resulting mixture was stirred overnight at room temperature and evaporated under reduced pressure. The deprotected compound was taken back twice into diethyl ether. The remaining solvent was removed under reduced pressure and dried to afford the title compound (21 mg, quantitative). LCMS (Method A): RT=3.87 min, M-16=383. 1H NMR (500 MHz, MeOD): 8.70 (1H, br s), 7.44-7.43 (4H,m), 7.30-7.28 (3H, m), 7.21-7.19 (2H, m), 4.63 (2H, t), 4.11 (2H, t), 2.75-2.70 (2H, m), 2.56-2.50 (2H, m), 2.42 (3H, s), 2.24-2.15 (1H, m), 1.97-1.88 (1H, m).

Workup

  1. customevaporated under reduced pressure
  2. customThe remaining solvent was removed under reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-30825ec25b4546779e12d0b258977484
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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