Diisopropylethylamine → HCID 71258839, compound

HRID 714402Notes

Reaction equation

HRID 714402 reaction equation
Br[C:2]1[N:6]=[C:5]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[CH2:9][CH2:8]2)[S:4][N:3]=1.Cl.[F:24][C:25]1([F:31])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>CN1CCCC1=O>[F:24][C:25]1([F:31])[CH2:30][CH2:29][N:28]([C:2]2[N:6]=[C:5]([N:7]3[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]4[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=4)[CH2:9][CH2:8]3)[S:4][N:3]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27583514,4-Difluoropiperidine hydrochlorideHCID 71187345HCID 71187345, compound

Product 1

HCID 71258839HCID 71258839, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 3-bromo-5-(4-(4-methoxyphenethyl)piperazin-1-yl)-1,2,4-thiadiazole (55 mg, 143 μmol), 4,4-difluoropiperidine hydrochloride (67.8 mg, 430 μmol) and DIPEA (185 mg, 251 μl, 1.43 mmol) in N-Methyl-2-pyrrolidinone (1 mL) was heated with microwave at 200° C. for 2.5 h. The amber reaction solution was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3 to yield after evaporation of the product containing fractions 41.8 mg (69%) of the title compound as off-white solid. MS (m/e): 424.2 (MH+).

Workup

  1. customThe amber reaction solution
  2. customwas purified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customto yield
  6. customafter evaporation of the product
  7. additioncontaining fractions 41.8 mg (69%) of the title compound as off-white solid

Sources & evidence

ORD record
ord-517b7579fa714ed19d7366b12f6c447e
Source dataset
uspto-grants-2015_11
Patent number
US09187440B2

Reaction notes

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