HCID 10342201, compound → HCID 10403876, compound

HRID 1613628Notes

Reaction equation

HRID 1613628 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][N:24]([CH3:27])[S:23]3(=[O:29])=[O:28])[CH:18]=2)[NH:13][CH:12]=1)=O)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][N:24]([CH3:27])[S:23]3(=[O:29])=[O:28])[CH:18]=2)[NH:13][CH:12]=1

Participants

4

Reactant 1

HCID 10342201HCID 10342201, compound

Product 1

HCID 10403876HCID 10403876, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Step 1 (916 mg) in anhydrous dichloromethane (15 ml) and trifluoroacetic acid (4.5 ml) was stirred at room temperature under a nitrogen atmosphere for 1 hour. Solvents were removed under vacuum and the residue was azeotroped with toluene-methanol. Flash chromatography of the crude product (silica gel, dichloromethane-methanol-ammonia, 90:10:1) gave 372 mg (59%) of the title compound as a colourless thick oil which solidified on standing; δH (250 MHz, CDCl3) 8.16 (1H, br s, indole N--H), 7.45 (1H, s, Ar--H), 7.28 (1H, d, J=8.3 Hz, Ar--H), 7.05 (1H, dd, J=8.3 and 1.5 Hz, Ar--H), 7.02 (1H, d, J=1.8 Hz, Ar--H), 3.35 (2H, dd, J=9.8 and 7.1 Hz, --CH2N--), 3.26 (4H, s, --NCH2CH2N-- ), 3.08--2.99 (4H, m, --CH2 --), 2.88 (2H, t, J=6.2 Hz, Ar--CH2CH2NH2), 2.75 (3H, s, --NMe); m/z (CI) 323 (M+ +1). (Found: m/z 323.1543. C15H23N4O2S requires: m/z 323.1542).

Workup

  1. customSolvents were removed under vacuum
  2. customthe residue was azeotroped with toluene-methanol

Sources & evidence

ORD record
ord-ffdc157b6dcd4338b011ecc323ca9a3c
Source dataset
uspto-grants-1993_03
Patent number
US05194440

Reaction notes

Loading…