Formaldehyde → HCID 68659054, compound

HRID 1984571Notes

Reaction equation

HRID 1984571 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[C:6]([NH:8][CH2:9][C:10]1[S:11][C:12]([S:15]([N:18]2[CH2:23][CH2:22][CH:21]([NH:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[CH:13][CH:14]=1)=[O:7].[CH3:39]CN(C(C)C)C(C)C.C=O.C([BH3-])#N.[Na+]>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[C:6]([NH:8][CH2:9][C:10]1[S:11][C:12]([S:15]([N:18]2[CH2:19][CH2:20][CH:21]([N:24]([CH3:39])[CH2:25][C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=3)[CH2:22][CH2:23]2)(=[O:17])=[O:16])=[CH:13][CH:14]=1)=[O:7]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 10188090HCID 10188090, compound

Product 1

HCID 68659054HCID 68659054, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the hydrochloride salt of 1 (50 mg, 0.08 mmol), DIEA (12 ul, 0.08 mmol), formaldehyde solution 37% aq. (32 ul, 0.4 mmol) and Sodiumcyanoborohydride (10 mg, 0.16 mmol) in THF were heated under reflux for 15 h, whereupon complete alkylation took place. The reaction was diluted with DCM and the inorganic salts were extracted with water. The crude was dried over MgSO4, and the solution was evaporated to dryness. The oily residue was taken up in THF, 1N HCl in ether was added slowly upon which colourless crystalls of compound 205 were formed (yield: 51 mg, 97%). Anal. HPLC: R.t=4.39 min (method b). M/Z APCI: 582.1 (M+1), 580.4 (M−1). The following compound was prepared in a similar fashion according to the example 205 described above:

Workup

  1. temperatureunder reflux for 15 h, whereupon complete alkylation
  2. extractionthe inorganic salts were extracted with water
  3. dry with materialThe crude was dried over MgSO4
  4. customthe solution was evaporated to dryness
  5. addition1N HCl in ether was added slowly upon which colourless crystalls of compound 205
  6. customwere formed (yield: 51 mg, 97%)
  7. customR.t=4.39 min (method b)
  8. customThe following compound was prepared in a similar fashion

Sources & evidence

ORD record
ord-136af5da996a445780abc10c1885112e
Source dataset
uspto-grants-2009_06
Patent number
US07544700B2

Reaction notes

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