Triethylamine → HCID 86661949, compound

HRID 1853140Notes

Reaction equation

HRID 1853140 reaction equation
[C:1]([O:5][C:6]([N:8]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:9]1[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:19]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:18]=3[N:17]=2)=[N:11][C:12](Br)=[CH:13][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH2:47]([NH2:50])[C:48]#[CH:49]>CN(C=O)C.C(OCC)(=O)C.I[Cu].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:50][CH2:47][C:48]#[C:49][C:12]1[N:11]=[C:10]([C:16]2[N:20]([C:21]([O:23][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:22])[C:19]3[CH:28]=[C:29]([CH3:32])[CH:30]=[CH:31][C:18]=3[N:17]=2)[C:9]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])=[N:14][CH:13]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 239041PropargylamineHCID 86661948HCID 86661948, compound

Product 1

HCID 86661949HCID 86661949, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-[3-[bis(tert-butoxycarbonyl)amino]-6-bromo-pyrazin-2-yl]-6-methyl-benzimidazole-1-carboxylate (1000 mg, 1.654 mmol), iodocopper (31.50 mg, 0.1654 mmol), Pd(PPh3)4 (191.1 mg, 0.1654 mmol), triethylamine (836.8 mg, 1.153 mL, 8.270 mmol) and prop-2-yn-1-amine (182.2 mg, 3.308 mmol) were stirred in DMF (5 mL) at ambient temperature for 2 hours. The reaction mixture was diluted with ethyl acetate the organic layer washed with water, brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by column chromatography eluting with 25/75 ethyl acetate/petroleum ether to give the sub-title compound as an off-white solid which was used directly in the next step with out further purification.

Workup

  1. washwashed with water, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with 25/75 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-9256889a54b446e28534dcdb6138b59c
Source dataset
uspto-grants-2015_02
Patent number
US08962631B2

Reaction notes

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