Trifluoroacetic acid → HCID 22048133, compound

HRID 1830588Notes

Reaction equation

HRID 1830588 reaction equation
FC(F)(F)C(O)=O.[NH:8]([C:15]1[C:20]([Br:21])=[CH:19][N:18]=[C:17]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[C:30][CH2:31][NH:32]C(OC(C)(C)C)=O)=[CH:25][CH:24]=2)[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[NH:8]([C:15]1[C:20]([Br:21])=[CH:19][N:18]=[C:17]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]#[C:30][CH2:31][NH2:32])=[CH:27][CH:28]=2)[N:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22048127HCID 22048127, compound

Product 1

HCID 22048133HCID 22048133, compoundYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.25 ml) was added to a solution of 4-anilino-5-bromo-2-{4-[3-(t-butoxycarbonylamino)-1-propynyl]anilino}pyrimidine (Method 25; 30 mg, 0.06 mmol) in DCM (1 ml). The solution was left to stand for 3 hours and volatile material was removed by evaporation. The residue was triturated with diethyl ether to give the product as a trifluoroacetate salt (25 mg, 81%). NMR: 4.0 (m, 2H), 7.2 (m, 2H), 7.4 (m, 2H), 7.5–7.7 (m, 4H), 7.8 (m, 1H), 8.2 (br s, 2H), 8.7 (s, 1H), 9.6 (s, 1H); MS (MH+): 394.3, 396.3.

Workup

  1. waitThe solution was left
  2. customvolatile material was removed by evaporation
  3. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-118d279cde35492f8a2f8b3e1a59e056
Source dataset
uspto-grants-2006_06
Patent number
US07067522B2

Reaction notes

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