Trifluoroacetic acid → HCID 178490001, compound

HRID 1627296Notes

Reaction equation

HRID 1627296 reaction equation
C(OC(=O)[N:7]=[C:8]([NH:47]C(OC(C)(C)C)=O)[NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([CH2:20][S:21][C:22]2[N:23]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:24]([C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([O:37][CH3:38])[CH:31]=3)([CH3:29])[CH3:28])=[CH:25][N:26]=2)=[C:15]([F:46])[CH:14]=1)(C)(C)C.[C:56]([OH:62])([C:58]([F:61])([F:60])[F:59])=[O:57]>C(Cl)Cl.CCOC(C)=O>[F:59][C:58]([F:61])([F:60])[C:56]([O-:62])=[O:57].[NH2:47][C:8]([NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([CH2:20][S:21][C:22]2[N:23]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)[C:24]([C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([O:37][CH3:38])[CH:31]=3)([CH3:29])[CH3:28])=[CH:25][N:26]=2)=[C:15]([F:46])[CH:14]=1)=[NH2+:7]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178489999HCID 178489999, compound

Product 1

HCID 178490001HCID 178490001, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl(tert-butoxycarbonylamino)(2-(4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-3,5-difluorophenoxy)ethylamino)methylenecarbamate (273 mg) in DCM (1 mL) was added TFA (5 mL). After 1 h the reaction mixture was diluted with EtOAc, washed with H2O, satd NaHCO3 and brine. The combined organic layers were concentrated and purified by preparative HPLC (30-100%, CH3CN/H2O with 0.05% TFA) to yield the title compound as a white solid (112 mg, 68%, 2 steps). 1HNMR (400 MHz, CD3CN) δ 8.01 (m, 1H), 7.20-7.13 (m, 2H), 6.99-6.94 (m, 2H), 6.88-6.78 (m, 2H), 6.57 (d, J=2.1 Hz, 1H), 6.55-6.48 (m, 3H), 6.44-6.38 (m, 2H), 4.08 (t, J=5.0 Hz, 2H), 3.92 (s, 2H), 3.71 (s, 3H), 3.52 (dd, J=10.6, 5.4 Hz, 2H), 1.49 (s, 6H); MS (EI) m/z 604.4 (MH+).

Workup

  1. washwashed with H2O
  2. concentrationThe combined organic layers were concentrated
  3. custompurified by preparative HPLC (30-100%, CH3CN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-96b1c343d218444bab577f623e7447f9
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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