2-Butanamine, 2-methyl- → HCID 22922542, compound

HRID 2258545Notes

Reaction equation

HRID 2258545 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][N:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22][CH2:23][CH3:24])=[CH:21][C:16]=3[N:15]([CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:14]2=[O:31])=[C:10]([O:34][CH3:35])[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=C[C:46]=2N=N1.CCN(C(C)C)C(C)C.C(N)(CC)(C)C>C(Cl)Cl>[CH:25]1([N:15]2[C:16]3[CH:21]=[C:20]([O:22][CH2:23][CH3:24])[CH:19]=[CH:18][C:17]=3[N:13]([CH2:12][C:11]3[CH:32]=[CH:33][C:8]([C:6](=[O:7])[NH:5][C:1]([CH3:4])([CH3:2])[CH2:3][CH3:46])=[CH:9][C:10]=3[O:34][CH3:35])[C:14]2=[O:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 689862-Butanamine, 2-methyl-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 229224911-[4-(N-tert-Butylcarbamoyl)-2-methoxybenzyl]-3-cyclohexyl-5-ethoxy-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 22922542HCID 22922542, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.9 g of the compound obtained in Example 15 Step B, 0.9 g of BOP and 1 ml of DIPEA in 20 ml of DCM is added 1 g of tert-amylamine, and the mixture is left stirring for 3 hours at RT. The reaction mixture is washed with 1N HCl solution, with 1N NaOH solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. The residue is chromatographed on silica, eluting with DCM. 0.34 g of the expected product is obtained, mp=164° C.

Workup

  1. waitthe mixture is left
  2. washThe reaction mixture is washed with 1N HCl solution, with 1N NaOH solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica
  6. washeluting with DCM

Sources & evidence

ORD record
ord-f55ae4b4c20a4304814809370b70318a
Source dataset
uspto-grants-1997_08
Patent number
US05661169

Reaction notes

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