Diisopropylethylamine → HCID 67302764, compound

HRID 1452943Notes

Reaction equation

HRID 1452943 reaction equation
[CH2:1]([C:3]1[CH:30]=[CH:29][C:6]([CH2:7][N:8]2[CH2:13][CH:12]3[CH:10]([CH:11]3[CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:18]([F:28])[CH:17]=3)[CH2:9]2)=[CH:5][CH:4]=1)[CH3:2].CCN(C(C)C)C(C)C.[S:40]1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2[CH:42]=[C:41]1[C:49](Cl)=[O:50].C([O-])(O)=O.[Na+]>ClCCCl>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH:12]3[CH:10]([CH:11]3[CH2:14][N:15]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:18]([F:28])[CH:17]=3)[C:49]([C:41]3[S:40][C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=4[CH:42]=3)=[O:50])[CH2:9]2)=[CH:29][CH:30]=1)[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 142384Benzo[b]thiophene-2-carbonyl ChlorideHCID 516892Sodium BicarbonateHCID 69033356HCID 69033356, compound

Product 1

HCID 67302764HCID 67302764, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirring solution of [3-(4-Ethyl-benzyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-(3-fluoro-4-morpholin-4-yl-phenyl)-amine prepared above (50 mg, 0.12 mmol) in 2 mL of DCE at room temperature was added DIEA (0.03 mL, 0.18 mmol) and 2-benzthiophenecarbonylchloride (0.02 mL, 0.18 mmol). After 1 hour, saturated NaHCO3 was added, and the mixture was extracted with CH2Cl2. The combined extracts were dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting crude material was taken up in 50% EtOAc/hexanes and the white solids were filtered off. The remaining filtrate was concentrated under reduce pressure to yield 58 mg of the desired product. 400 MHz 1H NMR (CDCl3) δ 7.60-7.68 (m, 2H), 7.24-7.31 (m, 2H),7.08-7.18 (m, 5H), 6.99-7.02 (m, 2H), 6.86-6.91 (m, 1H), 3.82-3.88 (m, 4H), 3.68 (d, J=7.47 Hz, 2H), 3.50 (brs, 2H), 3.10-3.12 (m, 4H), 2.88 (brd, J=7.47 Hz, 2H), 2.49 (q, 2H), 2.28, (brs, 2H), 1.49 (brs, 1H), 1.22-1.24 (m, 2H), 1.19 (t, 3H); MS (M+1) 570.2.

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. dry with materialThe combined extracts were dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe white solids were filtered off
  6. concentrationThe remaining filtrate was concentrated

Sources & evidence

ORD record
ord-84b2ae4e44cf4b9a8836ddcf540aa849
Source dataset
uspto-grants-2009_01
Patent number
US07473787B2

Reaction notes

Loading…