Acetic Anhydride → HCID 58550989, compound

HRID 1908171Notes

Reaction equation

HRID 1908171 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 calc. 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-25189e25c12b4041a78dfcb206faa048
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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