Triethylamine → HCID 25211713, compound

HRID 1409831Notes

Reaction equation

HRID 1409831 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[S:12][C:13]([C:16]3[C:20]([CH3:21])=[C:19]([C:22]([F:25])([F:24])[F:23])[O:18][N:17]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4]1.Cl.[CH3:27][N:28]([CH2:30][C:31](Cl)=[O:32])[CH3:29].C(N(CC)CC)C>C1COCC1>[CH3:27][N:28]([CH3:29])[CH2:30][C:31]([NH:2][C@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[S:12][C:13]([C:16]3[C:20]([CH3:21])=[C:19]([C:22]([F:25])([F:24])[F:23])[O:18][N:17]=3)=[CH:14][CH:15]=2)=[O:10])[CH2:4]1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 131729820HCID 131729820, compound

Product 1

HCID 25211713HCID 25211713, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ((S)-3-Amino-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone, hydrochloride (Example 26, 79 mg, 0.20 mmol) in THF (3 mL) was treated with dimethylaminoacetyl chloride hydrochloride (40 mg, 0.24 mmol) followed by triethylamine (62 μL, 0.44 mmol). The resulting mixture was stirred for 16 hr, evaporated to an oil, and dissolved in water (3 mL). The solution was then basified with a saturated aqueous K2CO3 solution and the precipitated product filtered, washed with water, and air dried to afford product as a colorless solid (69 mg, 78%). 1H NMR (CDCl3) 1.62-1.72 (m, 2 H), 1.78-1.84 (m, 1 H), 1.94-2.04 (m, 1 H), 2.25 (s, 6 H), 2.32 (d, J=1.3, 3 H), 2.49 (s, 2 H), 3.24-3.40 (m, 2 H), 3.94-4.04 (m, 2 H), 4.12 (br d, J=13.2, 1 H), 7.23 (br d, J=7.5, 1 H), 7.44 (d, J=4.0, 1 H), 7.47 (br s, 1 H). 13C NMR 7.9, 23.5, 30.4, 45.6, 46.2, ˜51 (br), 63.2, 114.8, 118.8 (q, J=271), 128.3, 129.5, 131.6, 140.2, 155.1 (q, J=40), 157.9, 163.1, 170.7. 19F NMR −63.1. LC/MS 4.59 min, [M+1]+ 445.

Workup

  1. customevaporated to an oil
  2. dissolutiondissolved in water (3 mL)
  3. filtrationthe precipitated product filtered
  4. washwashed with water, and air
  5. customdried

Sources & evidence

ORD record
ord-6c5a071ab529414dae47dd5cec27f22c
Source dataset
uspto-grants-2014_12
Patent number
US08921399B2

Reaction notes

Loading…