Diisopropylethylamine → HCID 46932710, compound

HRID 1192101Notes

Reaction equation

HRID 1192101 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[O:25]1[C:29]2[CH:30]=[CH:31][C:32]([CH2:34][NH2:35])=[CH:33][C:28]=2[CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.[Cl:45][C:46]1[CH:47]=[N:48][CH:49]=[C:50]([Cl:64])[C:51]=1[S:52][C:53]1[S:57][C:56]([C:58](O)=[O:59])=[CH:55][C:54]=1[N+:61]([O-:63])=[O:62]>ClCCl>[Cl:64][C:50]1[CH:49]=[N:48][CH:47]=[C:46]([Cl:45])[C:51]=1[S:52][C:53]1[S:57][C:56]([C:58]([NH:35][CH2:34][C:32]2[CH:31]=[CH:30][C:29]3[O:25][CH2:26][CH2:27][C:28]=3[CH:33]=2)=[O:59])=[CH:55][C:54]=1[N+:61]([O-:63])=[O:62]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27353672,3-Dihydro-1-benzofuran-5-ylmethanamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 602073175-((3,5-Dichloropyridin-4-yl)thio)-4-nitrothiophene-2-carboxylic acid

Product 1

HCID 46932710HCID 46932710, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(7-Aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (76.4 mg, 0.51 mmol), 2,3-dihydrobenzofuran-5-ylmethanamine (165.5 mg, 1.28 mmol) and diisopropylethylamine (12 mg, 0.12 mmol) was added to a suspension of 5-[(3,5-dichloro-4-pyridyl)sulfanyl]-4-nitro-thiophene-2-carboxylic acid (150 mg, 0.43 mmol) in dichloromethane (3 mL) and the resulting mixture was stirred at ambient temperature for 6 hours. TLC analysis showed no acid remaining so the mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried (Na2SO4), filtered and the solvent was removed to afford a solid. The crude material was purified by silica gel chromatography using a 70:30 mixture of hexane and ethyl acetate as eluent to afford the title product as a brown solid (11 mg, 5% yield). 1H NMR (400 MHz, d6-DMSO) δ: 9.28 (1H, m), 8.99 (2H, m), 8.46 (1H, s), 7.14 (1H, m), 7.00 (1H, m), 6.69 (1H, m), 4.48 (2H, m), 4.30 (2H, m), 3.15 (2H, m). MS m/z: 480.11, 482.11 [M+H]+.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed
  5. customto afford a solid
  6. customThe crude material was purified by silica gel chromatography
  7. additiona 70:30 mixture of hexane and ethyl acetate as eluent

Sources & evidence

ORD record
ord-1e8def445ae74304a2e87f50a9e26d66
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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