Triethylamine → HCID 58109221, compound

HRID 2037573Notes

Reaction equation

HRID 2037573 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C@@:5]1([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH3:13])[CH2:7][CH2:6]1.CCN(CC)CC.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>>[CH:14]1([C@@H:12]([N:8]2[CH2:7][CH2:6][C@:5]([CH2:4][CH2:3][CH2:2][NH:1][S:35]([CH3:34])(=[O:37])=[O:36])([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[O:10][C:9]2=[O:11])[CH3:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58109421HCID 58109421, compound

Product 1

HCID 58109221HCID 58109221, compoundYield 33%

Procedure

To a solution of (R)-6-(3-aminopropyl)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (30 mg, 0.10 mmol) was added Et3N (40 mg, 0.4 mmol) and MsCl (30 mg, 0.24 mmol) at 0° C. The reaction solution was stirred at rt for 2 h. The reaction was quenched by H2O and the mixture was extracted with CH2Cl2. The organic phase was concentrated to give the crude product, which was purified by preparative TLC to give N-(3-((R)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl)methanesulfonamide (11.5 mg, 33%). LC-MS Method 2 tR=1.397 min, m/z=440.9; 1H NMR (CDCl3) 1.04 (d, 6H), 1.13-1.34 (m, 2H), 1.43-1.68 (m, 6H), 1.73-1.98 (m, 3H), 2.03-2.14 (m, 1H), 2.29 (d, 1H), 2.52 (tt, 1H), 2.85 (s, 3H), 2.92-3.08 (m, 3H), 3.68 (m, 1H), 3.88-3.98 (m, 1H), 4.33 (t, 1H), 7.01 (t, 2H), 7.22 (m, 2H).

Workup

  1. customThe reaction was quenched by H2O
  2. extractionthe mixture was extracted with CH2Cl2
  3. concentrationThe organic phase was concentrated
  4. customto give the crude product, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-99f77b58d4ac4b69992f2b5c8774ac3a
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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