Formaldehyde → HCID 478200, compound

HRID 1005564Notes

Reaction equation

HRID 1005564 reaction equation
[C:1](=[O:29])([O:3][CH2:4][C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[C:7]([S:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=1)[NH2:2].[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.[CH2:36]=O>C(OCC)(=O)C>[O:33]1[CH2:34][CH2:35][N:30]([CH2:36][NH:2][C:1](=[O:29])[O:3][CH2:4][C:5]2[N:6]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:7]([S:13][C:14]3[CH:15]=[C:16]([Cl:21])[CH:17]=[C:18]([Cl:20])[CH:19]=3)=[C:8]([CH:10]([CH3:12])[CH3:11])[N:9]=2)[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1783CapravirineHCID 8083Morpholine

Product 1

HCID 478200HCID 478200, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the compound 111 (306 mg, 0.7 mmol), morpholine (61.0 mg, 0.7 mmol) and paraformaldehyde (22.0 mg, 0.733 mmol) in ethyl acetate (4 mL) was heated under reflux in an atmosphere of nitrogen for 3 days. After cooling down at room temperature, the residue was purified by chromatography on a silica gel column (eluate: ethyl acetate - methanol (5:1)) to give the compound 113 (265 mg, 69%). Rf 0.63 (5:1 EtOAc-CH3OH). 1H-NMR (CDCl3): δH1.30 (6 H, d, J 6.9 Hz, (CH3)2CH), 2.44 (4H, m, N(CH2CH2)2O), 3.18 (1 H, sep, J 6.9 Hz, (CH3)2CH), 3.65 (4 H, m, N(CH2CH2)2O), 3.91 (2 H, d, J 6.6 Hz, NCH2NH), 4.98 (1 H, t, J 6.6 Hz, NCH2NH ), 5.19 (2 H, s, CH2O), 5.25 (2 H, s, NCH2 ), 6.69 (2 H, d, J 1.8 Hz, arom 2- and 6-H), 6.71 (2 H, d-like, 4-pyridyl 2- and 6-H), 7.05 (1 H, t, J 1.8 Hz, arom 4-H), 8.45 (2 H, d-like, 4-pyridyl 3- and 5-H). Elementary analysis (for C25H29N5O2SCl2) Calcd. : C, 54.55% H, 5.31% N, 12.72% S, 5.82% Cl, 12.88% Found: C, 54.37% H, 5.36% N, 12.80% S, 5.92% Cl, 12.64% hydrochloride of 113 Elementary analysis (for C25H32N5O3SCl5 3HCl 3H2O) Calcd. : C, 42.06% H, 5.36% N, 9.81% S, 4.40% Cl, 24.83% Found: C, 42.01% H, 5.34% N, 10.01% S, 4.73% Cl, 24.92%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 3 days
  3. customthe residue was purified by chromatography on a silica gel column (eluate: ethyl acetate - methanol (5:1))

Sources & evidence

ORD record
ord-5141470d7d6a42cb810b2c8edb56de17
Source dataset
uspto-grants-2000_04
Patent number
US06054591

Reaction notes

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