2-Butanamine, 2-methyl- → HCID 23364234, compound

HRID 1081513Notes

Reaction equation

HRID 1081513 reaction equation
[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=1)[CH3:2].[CH3:34][C:35]([NH2:39])([CH3:38])[CH2:36][CH3:37].CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[CH2:1]([O:3][C:4]1[CH:33]=[CH:32][C:7]2[N:8]([S:18]([C:21]3[CH:29]=[CH:28][C:24]([C:25](=[O:27])[NH:39][C:35]([CH3:38])([CH3:34])[CH2:36][CH3:37])=[CH:23][C:22]=3[O:30][CH3:31])(=[O:20])=[O:19])[C:9](=[O:17])[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)[C:6]=2[CH:5]=1)[CH3:2]

Participants

6

Reactant 4

HCID 689862-Butanamine, 2-methyl-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23364252HCID 23364252, compound

Product 1

HCID 23364234HCID 23364234, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.3 g of the compound obtained in EXAMPLE 111 step B), 0.5 ml of 1,1-dimethylpropylamine, 0.5 ml of DIPEA, 0.35 g of BOP and 20 ml of DCM is stirred for 3 hours at RT. The reaction mixture is concentrated under vacuum, the residue is extracted with AcOEt, washed 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 a DCM/AcOEt mixture (90/10; v/v) as the eluent to give 0.15 g of the expected product after crystallization from iso ether.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe residue is extracted with AcOEt
  3. washwashed with a 1N solution of HCl and with a 1N solution of NaOH
  4. dry with materialdried over Na2SO4
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (90/10; v/v) as the eluent

Sources & evidence

ORD record
ord-c2e36a71115744e8a8465aa7f5e39cd5
Source dataset
uspto-grants-1996_12
Patent number
US05585394

Reaction notes

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