Acetic Anhydride → HCID 58550989, compound

HRID 2204266Notes

Reaction equation

HRID 2204266 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]2[C:8]3[CH:33]=[CH:32][CH:31]=[CH:30][C:9]=3[O:10][C:11]3([CH2:16][CH2:15][N:14]([C:17]([C:19]4[CH:24]=[CH:23][C:22]([O:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH3:29])[CH:20]=4)=[O:18])[CH2:13][CH2:12]3)[C:6]2=[CH:5][CH:4]=1.[C:34](OC(=O)C)(=[O:36])[CH3:35]>ClCCl.N1C=CC=CC=1>[CH:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:17]([N:14]2[CH2:15][CH2:16][C:11]3([O:10][C:9]4[CH:30]=[CH:31][CH:32]=[CH:33][C:8]=4[N:7]4[C:3]([CH2:2][NH:1][C:34](=[O:36])[CH3:35])=[CH:4][CH:5]=[C:6]34)[CH2:12][CH2:13]2)=[O:18])=[CH:20][C:21]=1[CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 54671219HCID 54671219, compound

Product 1

HCID 58550989HCID 58550989, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Crude (1-(aminomethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-isopropoxy-3-methylphenyl)methanone (49 mg, 0.11 mmol) was dissolved in a solution of dry dichloromethane (0.5 mL) and pyridine (0.3 mL) and was cooled to 0° C. Acetic anhydride (52 μL, 0.55 mmol) was added and the reaction mixture was stirred for 30 minutes. The reaction mixture was quenched by the addition of methanol (0.5 mL), concentrated, and purified by reverse phase HPLC [10-99% acetonitrile in water (HCl modifier)] to give N-((1′-(4-isopropoxy-3-methylbenzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-yl)methyl)acetamide. 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=7.9 Hz, 1H), 7.33-7.21 (m, 2H), 7.13 (d, J=4.2 Hz, 2H), 7.10-7.02 (m, 1H), 6.83 (d, J=8.1 Hz, 1H), 6.26 (d, J=3.4 Hz, 1H), 5.99 (d, J=3.5 Hz, 1H), 5.68 (s, 1H), 4.71 (d, J=4.7 Hz, 2H), 4.64-4.50 (m, 1H), 3.50 (s, 2H), 2.22 (s, 3H), 2.17-1.76 (m, 7H), 1.67 (s, 2H), 1.36 (d, J=6.0 Hz, 6H). ESI-MS m/z talc. 487.6, found 488.5 (M+1)+; Retention time: 1.81 minutes (3 min run).

Workup

  1. customThe reaction mixture was quenched by the addition of methanol (0.5 mL)
  2. concentrationconcentrated
  3. custompurified by reverse phase HPLC [10-99% acetonitrile in water (HCl modifier)]

Sources & evidence

ORD record
ord-549ee5b9128049e18d77a1a3ef322412
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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