Ethyl formate → HCID 58551581, compound

HRID 2204265Notes

Reaction equation

HRID 2204265 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[N:8]2[C:9]3[CH:34]=[CH:33][CH:32]=[CH:31][C:10]=3[O:11][C:12]3([CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:25]=[CH:24][C:23]([O:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH3:30])[CH:21]=4)=[O:19])[CH2:14][CH2:13]3)[C:7]2=[CH:6][CH:5]=1.[CH:35](OCC)=[O:36]>>[CH:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:18]([N:15]2[CH2:16][CH2:17][C:12]3([O:11][C:10]4[CH:31]=[CH:32][CH:33]=[CH:34][C:9]=4[N:8]4[C:4]([CH2:3][NH:2][CH:35]=[O:36])=[CH:5][CH:6]=[C:7]34)[CH2:13][CH2:14]2)=[O:19])=[CH:21][C:22]=1[CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 8025Ethyl formateHCID 67467446HCID 67467446, compound

Product 1

HCID 58551581HCID 58551581, compound

Procedure

A solution of (1-(aminomethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-isopropoxy-3-methylphenyl)methanone hydrochloride (60 mg, 0.13 mmol) in ethyl formate (109 μL, 1.35 mmol) was heated at 50° C. overnight. The solvent was removed under reduced pressure and the product was 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)formamide. 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.30-7.22 (m, 1H), 7.20-7.01 (m, 3H), 6.83 (d, J=8.1 Hz, 1H), 6.28 (d, J=3.5 Hz, 1H), 5.99 (d, J=3.6 Hz, 1H), 5.89 (s, 1H), 4.77 (d, J=5.0 Hz, 2H), 4.62-4.52 (m, 1H), 3.50 (s, 2H), 2.21 (s, 3H), 2.17-1.78 (m, 4H), 1.70 (s, 2H), 1.36 (d, J=6.0 Hz, 6H). ESI-MS m/z talc. 473.6, found 474.5 (M+1)+; Retention time: 1.80 minutes (3 min run).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was purified by reverse phase HPLC 10-99% acetonitrile in water (HCl modifier)

Sources & evidence

ORD record
ord-a68bcdaedf514e2dae3638adfbfc84dd
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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