Trifluoroacetic acid → HCID 73055730, compound

HRID 1055465Notes

Reaction equation

HRID 1055465 reaction equation
[C:1]([OH:7])([C:3]([F:6])([F:5])[F:4])=[O:2].[C:8]([C:10]1[N:11]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]#[N:53])[C:12]2[C:17]([C:18]=1[CH2:19][N:20]1[C:26](=[O:27])[C@@H:25]([NH:28][C:29](=[O:41])[C@@H:30]([N:32](C)[C:33](=O)OC(C)(C)C)[CH3:31])[CH2:24][O:23][C:22]3[CH:42]=[CH:43][CH:44]=[CH:45][C:21]1=3)=[CH:16][CH:15]=[CH:14][CH:13]=2)#[N:9].CC#N.O>C(Cl)Cl>[F:4][C:3]([F:6])([F:5])[C:1]([OH:7])=[O:2].[C:8]([C:10]1[N:11]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=2[C:52]#[N:53])[C:12]2[C:17]([C:18]=1[CH2:19][N:20]1[C:26](=[O:27])[C@@H:25]([NH:28][C:29](=[O:41])[C@@H:30]([NH:32][CH3:33])[CH3:31])[CH2:24][O:23][C:22]3[CH:42]=[CH:43][CH:44]=[CH:45][C:21]1=3)=[CH:16][CH:15]=[CH:14][CH:13]=2)#[N:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18373917Acetonitrile--water (1/1)HCID 131736366HCID 131736366, compound

Product 1

HCID 73055730HCID 73055730, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1.48 g, 1 mL, 13.0 mmol, Eq: 178) was added to a solution of tert-butyl (S)-1-((S)-5-((2-cyano-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepin-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (45 mg, 72.7 μmol, Eq: 1.00) in DCM (1.7 mL) at 0° C. After 1 h, the mixture was concentrated and the residue triturated with Et2O/Hexanes to give a solid which was lyophilized from MeCN/H2O to give the title compound (43 mg, 93.5%) as a solid. MS m/z 519 (MH+)

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue triturated with Et2O/Hexanes
  3. customto give a solid which

Sources & evidence

ORD record
ord-4b169a7d0a1d4bae952f33e5dcd3388f
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…