Triethylamine → HCID 71548452, compound

HRID 1184576Notes

Reaction equation

HRID 1184576 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]3[CH2:15][CH2:16][CH:17]([NH2:18])[CH:11]3[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][S:29](Cl)(=[O:31])=[O:30])=[CH:24][CH:23]=1.C(N(CC)CC)C>ClCCl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][S:29]([NH:18][C@H:17]2[C@@H:11]3[CH2:10][N:9]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:19])[F:20])[N:8]=4)[CH2:14][CH2:13][N:12]3[CH2:15][CH2:16]2)(=[O:31])=[O:30])=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 227304(4-Chlorophenyl)methanesulfonyl chlorideHCID 89466349HCID 89466349, compound

Product 1

HCID 71548452HCID 71548452, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 96B (100 mg, 0.349 mmol) in dry dichloromethane (2 mL) was added (4-chlorophenyl)methanesulfonyl chloride (118 mg, 0.524 mmol) and triethylamine (212 mg, 2.096 mmol). The mixture was stirred at room temperature for 16 hours and then concentrated. The residue was purified via HPLC (Gilson®, XBridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=254 nm) to give the title compound as the first eluting diastereomer. 1H NMR (500 MHz, methanol-d4) δ 1.57-1.66 (m, 1 H), 1.91-1.99 (m, 1 H), 2.21-2.29 (m, 2 H), 2.34 (q, 1H, J=8 Hz), 2.62 (dd, 1H, J=12, 10 Hz), 2.92 (td, 1H, J=12, 3 Hz), 3.00-3.06 (m, 2 H), 3.41 (td, 1H, J=9, 6 Hz), 4.33-4.40 (m, 3 H), 4.52 (dd, 1H, J=12, 1 Hz), 6.98 (t, 2H, J=7 Hz), 7.38-7.41 (m, 2 H), 7.44-7.48 (m, 2 H), 7.66-7.72 (m, 1 H); MS (DCI) m/z 475 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified via HPLC (Gilson®, XBridge™ 30×100 mm column, eluted with pH=10 aqueous ammonium bicarbonate-ammonium hydroxide/methanol, UV=254 nm)

Sources & evidence

ORD record
ord-41c1123d2b2741d0993d96c45917c6e7
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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