Triethylamine → HCID 76287263, compound

HRID 1050323Notes

Reaction equation

HRID 1050323 reaction equation
Cl.[CH:2]1([C:5]2[N:6]=[CH:7][C:8]([O:11][C@@H:12]3[CH2:22][N:15]4[C:16](=[O:21])[CH2:17][CH2:18][NH:19][CH2:20][C@H:14]4[CH2:13]3)=[N:9][CH:10]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[F:30][C:31]([F:43])([F:42])[C:32]1[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1>ClCCl>[CH:2]1([C:5]2[N:6]=[CH:7][C:8]([O:11][C@@H:12]3[CH2:22][N:15]4[C:16](=[O:21])[CH2:17][CH2:18][N:19]([S:38]([C:35]5[CH:34]=[CH:33][C:32]([C:31]([F:30])([F:42])[F:43])=[CH:37][CH:36]=5)(=[O:40])=[O:39])[CH2:20][C@H:14]4[CH2:13]3)=[N:9][CH:10]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 86723194HCID 86723194, compound

Product 1

HCID 76287263HCID 76287263, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(8S,9aR)-8-[(5-Cyclopropylpyrazin-2-yl)oxy]octahydro-5H-pyrrolo[1,2-a][1,4]diazepin-5-one hydrochloride (35 mg, 0.108 mmol, 1.0 equivalent, prepared as described in Example 46, Part H) was suspended in dichloromethane (1.0 mL) in a 4-mL scintillation vial. Triethylamine (32.7 mg, 0.323 mmol, 3.0 equivalents) was added followed by the addition of 4-(trifluoromethyl)benzene-1-sulfonyl chloride (34.3 mg, 0.140 mmol, 1.3 equivalents). The resulting solution was allowed to stir for 30 minutes at room temperature. The reaction solution was loaded directly onto a 4 g silica gel column and eluted with 0:100 to 50:50 ethyl acetate:heptanes (flow rate=18 mL/minute) over 20 minutes to give the title compound as a white solid (30 mg, 56%). 1H NMR (400 MHz, CDCl3) δ ppm 8.03 (d, J=1.3 Hz, 1H), 7.91 (dd, J=9.0, 4.9 Hz, 3H), 7.82 (d, J=8.4 Hz, 2H), 5.43 (t, J=3.9 Hz, 1H), 4.25 (dd, J=16.5, 9.6 Hz, 1H), 4.16-3.95 (m, 3H), 3.57 (dd, J=13.7, 4.0 Hz, 1H), 2.96-2.83 (m, 1H), 2.82-2.64 (m, 2H), 2.65-2.52 (m, 1H), 2.47 (dd, J=13.4, 9.3 Hz, 1H), 2.04-1.84 (m, 2H), 1.08-0.77 (m, 4H); MS (ESI+) m/z 497.0 (M+H)+; [a]D23.8=−0.15 (c=0.13, CH3OH).

Workup

  1. washeluted with 0:100 to 50:50 ethyl acetate

Sources & evidence

ORD record
ord-a6c5d7d399a84787a609e73c8d1bde7d
Source dataset
uspto-grants-2016_07
Patent number
US09382258B2

Reaction notes

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