Trifluoroacetic acid → 1-[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-6'-methylamino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469444Notes

Reaction equation

HRID 469444 reaction equation
C(O)(C(F)(F)F)=O.C(O[C:13](=O)[N:14]([C:16]1[N:21]=[C:20]([N:22]2[CH2:27][CH2:26][CH:25]([N:28]3[C:36]4[C:31](=[N:32][CH:33]=[CH:34][CH:35]=4)[NH:30][C:29]3=[O:37])[CH2:24][CH2:23]2)[CH:19]=[C:18]([C:38]([C:40]2[CH:50]=[C:49]([CH3:51])[C:43]3[N:44]([CH3:48])[C:45](=[O:47])[O:46][C:42]=3[CH:41]=2)=[O:39])[CH:17]=1)C)(C)(C)C>C(Cl)Cl>[CH3:48][N:44]1[C:43]2[C:49]([CH3:51])=[CH:50][C:40]([C:38]([C:18]3[CH:17]=[C:16]([NH:14][CH3:13])[N:21]=[C:20]([N:22]4[CH2:27][CH2:26][CH:25]([N:28]5[C:36]6[C:31](=[N:32][CH:33]=[CH:34][CH:35]=6)[NH:30][C:29]5=[O:37])[CH2:24][CH2:23]4)[CH:19]=3)=[O:39])=[CH:41][C:42]=2[O:46][C:45]1=[O:47]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58181138Tert-butyl[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl]-methyl-carbamate

Product 1

HCID 252676791-[4'-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-6'-methylamino-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl]-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 mL TFA were added to 59 mg (0.096 mmol) tert-butyl[4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl]-methyl-carbamate in 5.00 mL DCM and the mixture was stirred for 3 h at RT. Then the reaction mixture was evaporated down, the residue was dissolved in DMF and purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. customThen the reaction mixture was evaporated down
  2. dissolutionthe residue was dissolved in DMF
  3. custompurified by preparative HPLC-MS
  4. additionThe fractions containing the product
  5. customfreeze-dried

Sources & evidence

ORD record
ord-41a413ebde3e4d06816dc4c4b6b76862
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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