Formaldehyde → Trifluoroacetic acid

HRID 1012986Notes

Reaction equation

HRID 1012986 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[F:8][C:9]1[CH:33]=[CH:32][C:12]([CH2:13][NH:14][C:15]([C:17]2[N:18]=[C:19]3[C:25]([CH3:27])([CH3:26])[NH2+:24][CH2:23][CH2:22][CH2:21][N:20]3[C:28](=[O:31])[C:29]=2[OH:30])=[O:16])=[CH:11][CH:10]=1.C=O.C([BH3-])#N.[Na+]>>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH:14][C:15]([C:17]2[N:18]=[C:19]3[C:25]([CH3:27])([CH3:26])[N:24]([CH3:2])[CH2:23][CH2:22][CH2:21][N:20]3[C:28](=[O:31])[C:29]=2[OH:30])=[O:16])=[CH:32][CH:33]=1.[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67316496HCID 67316496, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 54698318HCID 54698318, compound

Procedure

A methanolic solution of 2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-10,10-dimethyl-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a][1,4]diazepin-9-ium trifluoroacetate (prepared as described in Example 9, Step 1-2) was treated with formaldehyde (1.5 eq.) and sodium cyanoborohydride (1.2 eq.). The mixture was stirred at room temperature 3 hours and then directly purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant) to give the title product as TFA salt, after lyophilization of the appropriate fractions.

Workup

  1. customdirectly purified by RP HPLC (C18, 5 μM, H2O/MeCN with 1% of TFA as eluant)

Sources & evidence

ORD record
ord-4a04b8b9807243e382533d4f13dee9e2
Source dataset
uspto-grants-2011_07
Patent number
US07981879B2

Reaction notes

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