Trifluoroacetic acid → HCID 90408110, compound

HRID 594088Notes

Reaction equation

HRID 594088 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[C:11](=[O:20])[N:10]([CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)[CH:9]=2)=[CH:6][C:5]([NH:31][C:32](=[O:43])[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][CH2:22][CH2:21][N:10]1[C:11](=[O:20])[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:13][C:8]([C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[C:5]([NH:31][C:32](=[O:43])[C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=3)[CH:6]=2)=[CH:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131734564HCID 131734564, compound

Product 1

HCID 90408110HCID 90408110, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0.1 M solution of tert-butyl (2-(2′-methyl-5-morpholino-6-oxo-5′-(3-(trifluoromethyl)benzamido)-[3,3′-bipyridin]-1(6H)-yl)ethyl)carbamate (1.00 equiv.) in 1:1 DCM:TFA was stirred for 15 min at ambient temperature. The reaction mixture was concentrated. The residue was basified with aqueous sodium carbonate and extracted with DCM. The combined extracts were dried over sodium sulfate, filtered, and concentrated to give crude N-(1′-(2-aminoethyl)-2-methyl-5′-morpholino-6′-oxo-1′,6′-dihydro-[3,3′-bipyridin]-5-yl)-3-(trifluoromethyl)benzamide which was used without further purification. LCMS (m/z) (M+H)=502.2, Rt=0.58 min.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with DCM
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3ad4d6be912346249d163d8bbc8473b7
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Reaction notes

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