Isobutylamine → HCID 178449297, compound

HRID 598207Notes

Reaction equation

HRID 598207 reaction equation
[C:1]([C:3]([C:14](=[O:29])[N:15]([CH:26]([CH3:28])[CH3:27])[C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([SH:23])[S:22][C:18]=2[CH:17]=1)=[CH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1)#[N:2].[CH2:30]([NH2:34])[CH:31]([CH3:33])[CH3:32].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>C1COCC1>[CH2:30]([NH:34][C:9](=[O:11])[C:8]1[CH:7]=[CH:6][C:5]([CH:4]=[C:3]([C:1]#[N:2])[C:14](=[O:29])[N:15]([CH:26]([CH3:27])[CH3:28])[C:16]2[CH:25]=[CH:24][C:19]3[N:20]=[C:21]([SH:23])[S:22][C:18]=3[CH:17]=2)=[CH:13][CH:12]=1)[CH:31]([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178457775HCID 178457775, compound

Product 1

HCID 178449297HCID 178449297, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combined 4-{2-Cyano-2-[isopropyl-(2-mercapto-benzothiazol-6-yl)-carbamoyl]-vinyl}benzoic acid (50 mg, 0.118 mmol), isobutylamine (13 μl, 0.130 mmol), HATU (58 mg, 0.153 mmol), and N,N-diisopropylethylamine (27 μl, 0.153 mmol) in anhydrous THF (1.1 ml). The mixture was stirred 2 hours, filtered through celite and concentrated in vacuo. The residue was partitioned between ethyl acetate and 1 M aqueous citric acid. The organic extract was dried over magnesium sulfate and purified by preparative TLC (10% methanol, 90% dichloromethane) to yield 28 mg (50%). 1H NMR (CDCl3) δ0.93 (d, 6H), 1.18 (d, 6H), 1.86 (m, 1H), 3.25 (t, 1H), 4.95 (m, 1H), 6.39 (t, 1H), 7.13 (dd, 1H), 7.24 (m, 3H), 7.72 (app q, 4H), 7.91 (s, 1H); ESIMS: m/z 477 (M-H).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 1 M aqueous citric acid
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. custompurified by preparative TLC (10% methanol, 90% dichloromethane)
  7. customto yield 28 mg (50%)

Sources & evidence

ORD record
ord-e9a0662c4d3c48d4a2432b095dd7c4b3
Source dataset
uspto-grants-2011_03
Patent number
US07897615B2

Reaction notes

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