Formaldehyde → HCID 68687774, compound

HRID 1172789Notes

Reaction equation

HRID 1172789 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[N:30]3[CH:31]=[CH:32][CH:33]=[C:29]3[C:28](=[O:34])[NH:27][CH:26]=2)=[CH:20][C:10]=1[C:11]([N:13]1[CH2:19][CH2:18][CH2:17][NH2+:16][CH2:15][CH2:14]1)=[O:12].C=O.[CH3:37]C([O-])=O.[Na+]>CO.O.CC#N>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[N:30]3[CH:31]=[CH:32][CH:33]=[C:29]3[C:28](=[O:34])[NH:27][CH:26]=2)=[CH:20][C:10]=1[C:11]([N:13]1[CH2:19][CH2:18][CH2:17][NH+:16]([CH3:37])[CH2:15][CH2:14]1)=[O:12]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 517045Sodium AcetateHCID 24872031HCID 24872031, compound

Product 1

HCID 68687774HCID 68687774, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of Example 1 in MeOH (0.1 M) was added TEA (2 eq), formaldehyde (5 eq), NaBH3(CN) (1.6 eq) and NaOAc (2.8 eq). The mixture was stirred overnight at RT and then the solvent was removed under reduced pressure and the product was isolated by purification at prep RP-HPLC using H2O (+0.1% TFA) and MeCN (+0.1% TFA) as eluents (C18 column). The desired fractions were lyophilized to afford the title compound. 1H NMR (600 MHz, DMSO-d6+TFA) (one major rotamer described) δ: 10.56-10.49 (1H, m), 9.78 (1H, br. S), 7.54-7.47 (1H, m), 7.44-7.37 (1H, m), 7.33-7.21 (2H, m), 6.88-6.93 (1H, m), 6.57-6.46 (2H, m), 4.08 (2H, s), 3.78-3.28 (6H, m, partially overlapped with D2O signal), 3.26-3.17 (2H, m), 2.85 (3H, s), 1.91-1.99 (2H, m). MS (ES) C21H23FN4O2 requires: 382, found: 383 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe product was isolated by purification at prep RP-HPLC

Sources & evidence

ORD record
ord-5ac3cfe4a26a4be4928d9a9be1839587
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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