Pyridine → HCID 68690004, compound

HRID 1172790Notes

Reaction equation

HRID 1172790 reaction equation
F[C:2](F)(F)[C:3]([O-])=[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].N1C=CC=CC=1.CC(OC(C)=O)=O>CO.O.CC#N>[C:3]([N:16]1[CH2:17][CH2:18][CH2:19][N:13]([C:11]([C:10]2[CH:20]=[C:21]([CH:22]=[CH:23][C:9]=2[F:8])[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)=[O:12])[CH2:14][CH2:15]1)(=[O:4])[CH3:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 24872031HCID 24872031, compound

Product 1

HCID 68690004HCID 68690004, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of Example 1 in MeOH was charged on SCX cartridge and washed with MeOH. The free base was then eluted with 2M NH3 in MeOH and the solvent removed under reduced pressure. The resulting amine was dissolved in THF and pyridine (2 eq) and Ac2O (1 eq) were added. The mixture was stirred for 1 h at RT and then the solvent was evaporated 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 (400 MHz, DMSO-d6+TFA) δ: 10.53-10.44 (1H, m), 7.51-7.36 (1H, m), 7.34-7.18 (3H, m), 6.91-6.87 (1H, m), 6.54-6.44 (2H, m), 4.09-4.02 (2H, m), 3.85-3.05 (8H, m, partially overlapped with D2O signal), 2.03-1.72 (3H, m), 1.43-1.15 (2H, m). MS (ES) C22H23FN4O3 requires: 410, found: 411 (M+H)+.

Workup

  1. washwashed with MeOH
  2. washThe free base was then eluted with 2M NH3 in MeOH
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe resulting amine was dissolved in THF
  5. customthe solvent was evaporated under reduced pressure
  6. customthe product was isolated by purification at prep RP-HPLC

Sources & evidence

ORD record
ord-f9209906bc9d40418b697a349e31e41d
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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