Acetonitrile → HCID 25005358, compound

HRID 925066Notes

Reaction equation

HRID 925066 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[C:28](=[O:35])[NH:27][N:26]=2)=[CH:20][C:3]=1[C:4]([N:6]1[CH2:12][CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5].FC(F)(F)C(O)=O.C(#N)C>ClCCl>[N:6]1([C:4]([C:3]2[CH:20]=[C:21]([CH:22]=[CH:23][C:2]=2[F:1])[CH2:24][C:25]2[C:34]3[CH2:33][CH2:32][CH2:31][CH2:30][C:29]=3[C:28](=[O:35])[NH:27][N:26]=2)=[O:5])[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 69090561HCID 69090561, compound

Product 1

HCID 25005358HCID 25005358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of EXAMPLE 5A (330 mg) in dichloromethane (8 mL) at 0° C. was added trifluoroacetic acid (8 mL). The solution was warmed to ambient temperature, and acetonitrile was added. The mixture was concentrated. The concentrate was purified by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0-100% acetonitrile/water with 0.1% trifluoroacetic acid). The product was dissolved in methanol/dichloromethane and treated with 1M hydrochloric acid in diethyl ether and filtered to give the title compound as the hydrochloride salt. 1H NMR (CD3OD) δ 1.70-1.76 (m, 4H), 2.02-2.11 (m, 2H), 2.52 (d, J=27.5 Hz, 4H), 3.32-3.36 (m, 2H), 3.40-3.46 (m, 2H), 3.51 (t, J=6.1 Hz, 2H), 3.95-4.01 (m, 2H), 4.06 (s, 2H), 7.19 (t, J=9.0 Hz, 1H), 7.29-7.34 (m, 1H), 7.36-7.41 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. customThe concentrate was purified by HPLC (Zorbax® C-18 ODS packing material [Agilent Technologies, Santa Clara, Calif.], 0-100% acetonitrile/water with 0.1% trifluoroacetic acid)
  3. dissolutionThe product was dissolved in methanol/dichloromethane
  4. additiontreated with 1M hydrochloric acid in diethyl ether
  5. filtrationfiltered

Sources & evidence

ORD record
ord-ad70d46317f34f14bfe7ac5f6177f1e6
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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