Diisopropylethylamine → HCID 86630208, compound

HRID 1170790Notes

Reaction equation

HRID 1170790 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:10][S:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][CH2:24][C:25]#[CH:26])[CH:20]=[CH:19][C:17]=3[N:18]=2)(=[O:13])=[O:12])=[CH:5][CH:4]=1.[N:41]([C@@H:44]([CH2:58][C:59]1[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][O:68][S:69]([C:72]2[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=2)(=[O:71])=[O:70])=[CH:61][CH:60]=1)[C:45]([N:47]1[CH2:52][CH2:51][CH:50]([C:53]([O:55][CH2:56][CH3:57])=[O:54])[CH2:49][CH2:48]1)=[O:46])=[N+:42]=[N-:43].C(N(C(C)C)CC)(C)C>C1COCC1.[Cu]I>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:10][S:11]([C:14]2[S:15][C:16]3[CH:22]=[C:21]([O:23][CH2:24][C:25]4[N:43]=[N:42][N:41]([C@@H:44]([CH2:58][C:59]5[CH:64]=[CH:63][C:62]([O:65][CH2:66][CH2:67][O:68][S:69]([C:72]6[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=6)(=[O:71])=[O:70])=[CH:61][CH:60]=5)[C:45]([N:47]5[CH2:48][CH2:49][CH:50]([C:53]([O:55][CH2:56][CH3:57])=[O:54])[CH2:51][CH2:52]5)=[O:46])[CH:26]=4)[CH:20]=[CH:19][C:17]=3[N:18]=2)(=[O:13])=[O:12])=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 59552483HCID 59552483, compoundHCID 86630207HCID 86630207, compound

Product 1

HCID 86630208HCID 86630208, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a stirring solution of N-(bis(4-methoxyphenyl)(phenyl)methyl)-6-(prop-2-ynyloxy)benzo[d]thiazole-2-sulfonamide (91 mg, 0.159 mmol) and the tosylate 145 (87 mg, 0.159 mmol) in THF (1 mL) was added copper(I) iodide (3 mg, 0.0159 mmol) then diisopropylethylamine (30 μL, 0.175 mmol). The mixture was allowed to stir for 2 h at 23° C. then concentrated in vacuo and the crude residue purified by flash chromatography on silica gel using hexanes/ethyl acetate on a Biotage purification system yielding the desired product as a white, crystalline solid (145 mg, 82%).

Workup

  1. concentrationthen concentrated in vacuo
  2. customthe crude residue purified by flash chromatography on silica gel
  3. customon a Biotage purification system

Sources & evidence

ORD record
ord-c1e5e4c60ef84117b7dea1bc58834034
Source dataset
uspto-grants-2010_11
Patent number
US07829063B2

Reaction notes

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