Trifluoroacetic acid → HCID 68671787, compound

HRID 512958Notes

Reaction equation

HRID 512958 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:57]=[C:58]([F:60])[CH:59]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[N:10]=[C:9]2[NH:34][C:35](=[O:56])[C:36]1[CH:41]=[C:40]([C:42]([N:44]2[CH2:48][CH2:47][CH2:46][C@H:45]2[CH2:49][N:50]2[CH2:54][CH2:53][CH2:52][CH2:51]2)=[O:43])[CH:39]=[CH:38][C:37]=1[F:55].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:57]=[C:58]([F:60])[CH:59]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:34][C:35](=[O:56])[C:36]1[CH:41]=[C:40]([C:42]([N:44]2[CH2:48][CH2:47][CH2:46][C@H:45]2[CH2:49][N:50]2[CH2:54][CH2:53][CH2:52][CH2:51]2)=[O:43])[CH:39]=[CH:38][C:37]=1[F:55]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68671686HCID 68671686, compound

Product 1

HCID 68671787HCID 68671787, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[5-(3,5-Difluoro-benzyl)-1-trityl-1H-indazol-3-yl]-2-fluoro-5-((S)-2-pyrrolidin-1-ylmethyl-pyrrolidine-1-carbonyl)-benzamide (90 mg, 0.112 mmol) in DCM (1 mL) was treated with TFA (0.17 mL, 2.24 mmol). After two hours at room temperature, DCM was added (25 mL) and the organic phase was washed with aqueous NaHCO3, water and brine. Drying over sodium sulphate, evaporation and purification of the crude over silica gel (eluent: DCM, MeOH, 7N NH3 in MeOH 9:1:0.1) afforded 42 mg of title compound.

Workup

  1. washthe organic phase was washed with aqueous NaHCO3, water and brine
  2. dry with materialDrying over sodium sulphate, evaporation and purification of the crude over silica gel (eluent: DCM, MeOH, 7N NH3 in MeOH 9:1:0.1)

Sources & evidence

ORD record
ord-1bc3df4c76be422bb39d6607fb12356a
Source dataset
uspto-grants-2015_08
Patent number
US09102662B2

Reaction notes

Loading…