tert-Octylamine → HCID 23364245, compound

HRID 1081502Notes

Reaction equation

HRID 1081502 reaction equation
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[C:6]=2[CH:5]=1)[CH3:2].[CH3:34][C:35]([NH2:42])([CH3:41])[CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:11]1([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:33]=[CH:32][C:7]=3[N:8]([S:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH:42][C:35]([CH3:41])([CH3:34])[CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9]2=[O:17])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 61017tert-OctylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 152290425-Ethoxy-1,3-dihydro-1-(2-methoxy-4-carboxybenzenesulfonyl)-3-cyclohexyl-2H-benzimidazol-2-one

Product 1

HCID 23364245HCID 23364245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.620 g of the compound obtained in EXAMPLE 13, 1 ml of 1,1,3,3-tetramethylbutylamine, 0.7 g of BOP, 1 ml of DIPEA and 20 ml of DCM is stirred for 2 hours at RT. The reaction mixture is then washed with water, with a 1N solution of HCl and with a 1N solution of NaOH and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using DCM as the eluent to give 0.28 g of the expected product in the form of white crystals. M.p.=180° C.

Workup

  1. washThe reaction mixture is then washed with water, with a 1N solution of HCl and with a 1N solution of NaOH
  2. dry with materialdried over Na2SO4
  3. customthe solvent is evaporated off under vacuum
  4. customThe residue is chromatographed on silica

Sources & evidence

ORD record
ord-22543f02b03b4f51b8994e8c9f0140f0
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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