Diisopropylethylamine → 3-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide

HRID 2096247Notes

Reaction equation

HRID 2096247 reaction equation
[C:1]([S:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27][NH2:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH:38]=1)[C:33](O)=[O:34].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH:38]=1)[C:33]([NH:28][CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[S:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:34]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222381233-Fluoro-5-(morpholin-4-yl)benzoic acidHCID 668224941-[2-(Tritylsulfanyl)phenyl]methanamine

Product 1

HCID 668228043-Fluoro-5-(morpholin-4-yl)-N-[2-(tritylsulfanyl)benzyl]benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 1-[2-(tritylsulfanyl)phenyl]methanamine (335 mg, 0.88 mmol), 3-fluoro-5-morpholin-4-yl-benzoic acid (WO2004/089929) (237 mg, 1.05 mmol) and DIPEA (0.38 mL, 2.19 mmol) in DMF (15 mL) was treated with HATU (400 mg, 1.05 mmol). The mixture was stirred at RT for 45 min, then partitioned between aqueous saturated NaHCO3 and EtOAc. The organic layer was separated, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo to afford the title compound (quantitative) as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.35-7.29 (6H, m), 7.27-7.19 (10H, m), 7.17 (2H, m), 7.10 (1H, t, J 1.7), 6.98-6.92 (1H, m), 6.73-6.64 (2H, m), 5.98 (1H, br t, J 6), 4.21 (2H, d, J 6), 3.84 (4H, t, J 4.8), 3.19 (4H, t, J 4.8).

Workup

  1. custompartitioned between aqueous saturated NaHCO3 and EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b76bae7d33e549c1bba53e7ac69457e1
Source dataset
uspto-grants-2013_05
Patent number
US08450314B2

Reaction notes

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