Trifluoroacetaldehyde → HCID 178425370, compound

HRID 642828Notes

Reaction equation

HRID 642828 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([CH3:41])[C:38]([NH2:42])=[C:37]([NH2:43])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:44]=[CH:45][CH:46]=[CH:47][C:4]=2[NH:3]1.[F:48][C:49]([F:53])([F:52])[CH:50]=O>CN(C=O)C.C(O)(C(F)(F)F)=O>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([CH3:41])[C:38]4[NH:42][C:50]([C:49]([F:53])([F:52])[F:48])=[N:43][C:37]=4[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:44]=[CH:45][CH:46]=[CH:47][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 65564TrifluoroacetaldehydeHCID 11549165HCID 11549165, compound

Product 1

HCID 178425370HCID 178425370, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 120 mg (0.16 mmol) (R)-1-(3,4-diamino-5-methyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate in 1 mL DMF was combined with 30 mg (0.26 mmol) trifluoroacetaldehyde and 3 drops of TFA and stirred for 2 h at 100° C. The residue was purified by HPLC, the fractions containing the product were combined and lyophilised.

Workup

  1. customThe residue was purified by HPLC
  2. additionthe fractions containing the product

Sources & evidence

ORD record
ord-107d5e9541ea423183344dfcfec055c5
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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