Isobutylamine → HCID 178449297, compound

HRID 1181611Notes

Reaction equation

HRID 1181611 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), 724 (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-53c7f5e6688946d2aaa7246f5674b52a
Source dataset
uspto-grants-2007_10
Patent number
US07285562B2

Reaction notes

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