Trifluoroacetic acid → HCID 58181103, compound

HRID 469441Notes

Reaction equation

HRID 469441 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:33][CH2:32][C:31]4[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:30]=4[NH:29][C:28]3=[O:40])[CH2:23][CH2:22]2)[CH:18]=[C:17]([C:41]([C:43]2[CH:53]=[C:52]([CH3:54])[C:46]3[N:47]([CH3:51])[C:48](=[O:50])[O:49][C:45]=3[CH:44]=2)=[O:42])[CH:16]=1)(C)(C)C>C(Cl)Cl>[NH2:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:33][CH2:32][C:31]4[CH:34]=[C:35]([O:38][CH3:39])[CH:36]=[CH:37][C:30]=4[NH:29][C:28]3=[O:40])[CH2:23][CH2:22]2)[CH:18]=[C:17]([C:41]([C:43]2[CH:53]=[C:52]([CH3:54])[C:46]3[N:47]([CH3:51])[C:48](=[O:50])[O:49][C:45]=3[CH:44]=2)=[O:42])[CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58181169HCID 58181169, compound

Product 1

HCID 58181103HCID 58181103, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.50 mL TFA were added to 57 mg (0.10 mmol) tert-butyl[4′-(3,4-dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-benzo[d][1,3]diazepin-3-yl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl]-carbamate in 5.00 mL DCM and stirred for 3 h at RT. Then another 0.50 mL TFA were added and the mixture was stirred overnight 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. stirringthe mixture was stirred overnight at RT
  2. customThen the reaction mixture was evaporated down
  3. dissolutionthe residue was dissolved in DMF
  4. custompurified by preparative HPLC-MS
  5. additionThe fractions containing the product
  6. customfreeze-dried

Sources & evidence

ORD record
ord-a1fb79a51a3a4ff2a4a483807484aec8
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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