Trifluoroacetic acid → HCID 71254688, compound

HRID 540256Notes

Reaction equation

HRID 540256 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][N:11]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][CH2:31][NH:32]C(=O)OC(C)(C)C)[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:40])[CH:25]=3)[N:20]=2)[CH2:10][CH2:9]1>ClCCl>[S:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][N:11]([C:19]2[N:28]=[C:27]([NH:29][CH2:30][CH2:31][NH2:32])[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([CH3:40])[CH:25]=3)[N:20]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86691424HCID 86691424, compound

Product 1

HCID 71254688HCID 71254688, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution of trifluoroacetic acid in dichloromethane (2 mL, V/V=1/4) was added tert-butyl {2-[2-(2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinazolin-4-yl]aminoethyl}carbamate (120 mg, 0.258 mmol) in an ice bath. The mixture was stirred for 3 hours whilst allowing the temperature of the mixture rising naturally to room temperature, and then concentrated in vacuo. The residue was dissolved in water (10 mL), and washed with dichloromethane (10 mL). The aqueous layer was adjusted to pH 10 with a saturated aqueous solution of sodium carbonate and extracted with ethyl acetate (20 mL×2). The organic extracts were dried with sodium sulfate, concentrated in vacuo to afford 68 mg of the product as a white solid (yield was 72%). MS obsd. (ESI+) [(M+H)+] 366, 1H NMR (400 MHz, CD3OD) δ ppm 7.67-7.64 (t, J=12.0 Hz, 2 H), 7.49-7.47 (d, J=8.4 Hz, 1 H), 7.38-7.30 (m, 2 H), 7.23-7.19 (dd, J=8.4, 7.6 Hz, 2 H), 7.13-7.09 (dd, J=8.8 Hz, 1 H), 5.04 (s, 2 H), 4.38 (s, 2 H), 3.75-3.72 (m, 2 H), 2.98-2.92 (m, 4 H), 2.39 (s, 3 H).

Workup

  1. customrising naturally to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (10 mL)
  4. washwashed with dichloromethane (10 mL)
  5. extractionextracted with ethyl acetate (20 mL×2)
  6. dry with materialThe organic extracts were dried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f7c29bb9d9e4214a8c3bc5371b7300f
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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