Trifluoroacetic acid → HCID 68671787, compound

HRID 1773392Notes

Reaction equation

HRID 1773392 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-534ef490991941559a52aa461b6d22e5
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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