Formaldehyde → HCID 66758834, compound

HRID 564217Notes

Reaction equation

HRID 564217 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[NH:16][C:15]4[CH:17]=[CH:18][CH:19]=[C:20]([C:21]([NH2:23])=[O:22])[C:14]=4[N:13]=3)[N:11]=2)[CH2:3][CH2:2]1.C=O.[C:26]([BH3-])#N.[Na+]>CO.O.[Cl-].[Zn+2].[Cl-]>[CH3:26][N:1]1[CH2:2][CH2:3][CH:4]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[NH:16][C:15]4[CH:17]=[CH:18][CH:19]=[C:20]([C:21]([NH2:23])=[O:22])[C:14]=4[N:13]=3)[N:11]=2)[CH2:5][CH2:6]1

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66759803HCID 66759803, compound

Product 1

HCID 66758834HCID 66758834, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of EXAMPLE 5 (50 mg) in methanol (8 mL) was added 37 wt % formaldehyde in water (28 μL) and TEA (21 μL). The solution was stirred for 1 hour, treated with sodium cyanoborohydride (28 mg) and zinc (II) chloride (20 mg), stirred for 60 hours and was concentrated. The concentrate was purified by HPLC (Zorbax C-8, 0.1% TFA/acetonitrile/water). The salt was dissolved in dichloromethane (2 mL) and methanol (2 mL), treated with 1M hydrochloric acid in ether (4 mL) and concentrated. 1H NMR (DMSO-d6) δ 2.12-2.23 (m, 2H), 2.32-2.41 (m, 2H), 2.78 (d, J=4.6 Hz, 3H), 3.10-3.20 (m, 2H), 3.41-3.48 (m, 1H), 3.50-3.59 (m, 2H), 7.45 (t, J=7.8 Hz, 1H), 7.80-7.82 (m, 1H), 7.82-7.85 (m, 1H), 7.94 (d, J=6.7 Hz, 1H), 8.82 (brs, 1H), 8.98 (brs, 1H), 10.84 (brs, 1H).

Workup

  1. stirringstirred for 60 hours
  2. concentrationwas concentrated
  3. customThe concentrate was purified by HPLC (Zorbax C-8, 0.1% TFA/acetonitrile/water)
  4. dissolutionThe salt was dissolved in dichloromethane (2 mL)
  5. additionmethanol (2 mL), treated with 1M hydrochloric acid in ether (4 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-be1547a0600e4aec9317d73d45e7bd2a
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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