Acetonitrile → HCID 67442449, compound

HRID 389942Notes

Reaction equation

HRID 389942 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:25]4[C:33]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[N:27]([S:34]([C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)(=[O:36])=[O:35])[CH:26]=4)[CH:23]=3)[C:18](=[O:43])[NH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(#N)C>ClCCl>[C:37]1([S:34]([N:27]2[C:28]3=[N:29][CH:30]=[CH:31][CH:32]=[C:33]3[C:25]([C:22]3[CH:23]=[C:24]4[C:19](=[CH:20][CH:21]=3)[C:18](=[O:43])[NH:17][N:16]=[C:15]4[CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:26]2)(=[O:35])=[O:36])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 67442198HCID 67442198, compound

Product 1

HCID 67442449HCID 67442449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 9B (272 mg, 0.45 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (1 mL) at ambient temperature for 1 hour. Acetonitrile (10 mL) was added and the solution was concentrated on a rotary evaporator. The residue was purified by HPLC (Zorbax C-18, 0-100% gradient of acetonitrile in water containing 0.1% trifluoroacetic acid) to yield the title compound. MS (ESI) m/z 500 (M+H)+; 1H NMR (300 MHz, CD3OD) δ 1.49-1.66 (m, 2H), 2.01-2.16 (m, 2H), 2.26-2.37 (m, 1H), 2.93-3.05 (m, 2H), 3.10 (d, J=7.12 Hz, 2H), 3.39 (d, J=12.54 Hz, 2H), 7.41 (dd, J=8.14, 4.75 Hz, 1H), 7.55-7.61 (m, 2H), 7.64-7.72 (m, 1H), 8.18-8.24 (m, 3H), 8.24-8.27 (m, 1H), 8.33 (dd, J=7.97, 1.53 Hz, 1H), 8.39 (s, 1H), 8.45 (dd, J=4.92, 1.53 Hz, 1H), 8.47-8.52 (m, 1H).

Workup

  1. concentrationthe solution was concentrated on a rotary evaporator
  2. customThe residue was purified by HPLC (Zorbax C-18, 0-100% gradient of acetonitrile in water containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-4d31a21a508142d6b66ecd12a700c06e
Source dataset
uspto-grants-2013_02
Patent number
US08383623B2

Reaction notes

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