Formaldehyde → HCID 135797755, compound

HRID 1350534Notes

Reaction equation

HRID 1350534 reaction equation
[C:1](O)(=O)CCC(O)=O.[F:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:17]=3[C:16]([N:28]3[CH2:33][CH2:32][NH:31][CH:30]([CH2:34][CH2:35][C:36]4[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=4)[CH2:29]3)=[N:15][C:14]=2[CH:44]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClCCl.[Cl-].[Na+]>[F:9][C:10]1[CH:11]=[CH:12][C:13]2[NH:19][C:18]3[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:23][C:17]=3[C:16]([N:28]3[CH2:33][CH2:32][N:31]([CH3:1])[CH:30]([CH2:34][CH2:35][C:36]4[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=4)[CH2:29]3)=[N:15][C:14]=2[CH:44]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 135797756HCID 135797756, compound

Product 1

HCID 135797755HCID 135797755, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve the free base obtained from Example 609 (0.078 g, 0.16 mmol) in dichloromethane (8 ml). Add sodium triacetoxyborohydride (0.066 g, 0.31 mmol) and formaldehyde (0.005 g, 0.16 mmol, 0.013 g of a 37% aqueous solution) and stir the mixture for two hours at ambient temperature. Dilute the mixture with saturated aqueous sodium chloride (50 mL) and extract three times with dichloromethane. Combine the organic layers, dryover sodium sulfate and remove the solvent under reduced pressure. Purification via flash chromatography, eluting with a linear gradient starting with 100% of a stock mixture of 80% dichloromethane with 20% hexanes and going to 85% of the stock mixture with 15% 2M ammonia in methanol, gives the free base of the title compound (0.062 g, 0.12 mmol, 77% yield) as a yellow amorphous solid. It is then converted to the succinate salt as described previously: Mass Spectrum (m/e): 513(M+1); Exact Mass Spec: Calc. 513.2278; Found 513.2284.

Workup

  1. extractionextract three times with dichloromethane
  2. customCombine the organic layers, dryover sodium sulfate and remove the solvent under reduced pressure
  3. customPurification via flash chromatography
  4. washeluting with a linear gradient

Sources & evidence

ORD record
ord-b8cad1ab002b47cf938ecbcf8d05f80e
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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