Triethylamine → HCID 44581704, compound

HRID 971154Notes

Reaction equation

HRID 971154 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][C:18]4[C:21]([C:32]([F:35])([F:34])[F:33])=[N:22][N:23]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)[C:17]=4[C:16]3=[O:36])=[CH:11][CH:10]=2)[CH2:8][CH2:7]1.CCN(CC)CC.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>C(Cl)Cl>[CH3:44][S:45]([N:3]1[CH2:4][CH2:5][N:1]=[C:2]1[C:6]1([C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:20][CH2:19][C:18]4[C:21]([C:32]([F:33])([F:34])[F:35])=[N:22][N:23]([C:24]5[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=5)[C:17]=4[C:16]3=[O:36])=[CH:13][CH:14]=2)[CH2:7][CH2:8]1)(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44581664HCID 44581664, compound

Product 1

HCID 44581704HCID 44581704, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 144 (0.017 g, 0.034 mmol) from was dissolved in CH2Cl2 (0.3 mL). Et3N (0.1 mL, 0.07 mmol) and MsCl (0.07 mL, 0.09 mmol) were added at rt under N2. The reaction was stirred for 12 h, concentrated to dryness, and purified via flash chromatography (silica, 100% EtOAc then 0.5% Et3N:10% MeOH:CH2Cl2) to afford the title compound. LC/MS (ESI+) 574.4 (M+H)+, tR=2.84 min (10–90% CH3CN/H2O in a 4-min run). 1H NMR ((CD3)2CO, 300 MHz) δ 7.50 (d, J=9.1 Hz, 2H), 7.33 (m, 4H), 6.98 (d, J=9.1 Hz, 2H), 4.16 (t, J=6.6 Hz, 2H), 3.83 (m, 7H), 3.16 (t, J=6.4 Hz, 2H), 2.42 (s, 3H), 1.47 (m, 2H), 1.18 (m, 2H) ppm.

Workup

  1. concentrationconcentrated to dryness
  2. custompurified via flash chromatography (silica, 100% EtOAc

Sources & evidence

ORD record
ord-faacf4821c1c4256b4cb63fecf5c75c8
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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