Diisopropylethylamine → HCID 86630209, compound

HRID 1803826Notes

Reaction equation

HRID 1803826 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]([CH2:71][C:72]1[CH:77]=[CH:76][C:75]([O:78][CH2:79][CH2:80][O:81][S:82]([C:85]2[CH:91]=[CH:90][C:88]([CH3:89])=[CH:87][CH:86]=2)(=[O:84])=[O:83])=[CH:74][CH:73]=1)[C:45]([N:47]([C@@H:55]([CH2:60][C:61]1[CH:66]=[CH:65][C:64]([C:67]([F:70])([F:69])[F:68])=[CH:63][CH:62]=1)[C:56]([O:58][CH3:59])=[O:57])[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[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]([CH2:71][C:72]5[CH:73]=[CH:74][C:75]([O:78][CH2:79][CH2:80][O:81][S:82]([C:85]6[CH:91]=[CH:90][C:88]([CH3:89])=[CH:87][CH:86]=6)(=[O:84])=[O:83])=[CH:76][CH:77]=5)[C:45]([N:47]([C@@H:55]([CH2:60][C:61]5[CH:62]=[CH:63][C:64]([C:67]([F:70])([F:69])[F:68])=[CH:65][CH:66]=5)[C:56]([O:58][CH3:59])=[O:57])[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[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 59621025HCID 59621025, compound

Product 1

HCID 86630209HCID 86630209, 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 (83 mg, 0.145 mmol) and the Boc-protected amide 151 (107 mg, 0.145 mmol) in THF (0.7 mL) was added copper(I) iodide (3 mg, 0.0145 mmol) then diisopropylethylamine (28 μL, 0.16 mmol). The mixture was allowed to stir for 2 h at 23° C. then concentrated in vacuo and the crude residue purified by flash chromatgraphy on silica gel using hexanes/ethyl actetate on a Biotage purification system yielding the desired product as a yellow, crystalline solid (145 mg, 82%).

Workup

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

Sources & evidence

ORD record
ord-cd5ea910c9404e15a4a601669386a99e
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

Loading…