Triethylamine → (2S)-3,3-dimethyl-2-({4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoyl}amino)butanoic acid dihydrochloride

HRID 500169Notes

Reaction equation

HRID 500169 reaction equation
C(N(CC)CC)C.[ClH:8].Cl.[N:10]1[C:19]2[C:14](=[CH:15][C:16]([C:20]3([C:23]4[N:27]5[CH:28]=[C:29]([C:32]6[CH:40]=[CH:39][C:35]([C:36](O)=[O:37])=[CH:34][CH:33]=6)[CH:30]=[N:31][C:26]5=[N:25][CH:24]=4)[CH2:22][CH2:21]3)=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.Cl.[NH2:42][C@@H:43]([C:51]([CH3:54])([CH3:53])[CH3:52])[C:44]([O:46]C(C)(C)C)=[O:45].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>[ClH:8].[ClH:8].[CH3:54][C:51]([CH3:52])([CH3:53])[C@H:43]([NH:42][C:36](=[O:37])[C:35]1[CH:39]=[CH:40][C:32]([C:29]2[CH:30]=[N:31][C:26]3[N:27]([C:23]([C:20]4([C:16]5[CH:15]=[C:14]6[C:19](=[CH:18][CH:17]=5)[N:10]=[CH:11][CH:12]=[CH:13]6)[CH2:22][CH2:21]4)=[CH:24][N:25]=3)[CH:28]=2)=[CH:33][CH:34]=1)[C:44]([OH:46])=[O:45]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 56776989tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochlorideHCID 672233294-[3-(1-Quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid dihydrochloride

Product 1

HCID 67224840(2S)-3,3-dimethyl-2-({4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoyl}amino)butanoic acid dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (230 μL) was added to a mixture of 4-[3-(1-quinolin-6-ylcyclopropyl)imidazo[1,2-a]pyrimidin-6-yl]benzoic acid dihydrochloride (162 mg, 0.339 mmol), tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride (75.8 mg, 0.339 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (165 mg, 0.373 mmol) in methylene chloride (10 mL). The mixture was stirred at RT for 3 h, washed with NaHCO3 (7.5%) and brine, dried over Na2SO4, filtered, and concentrated. The residue [LCMS: (M+H)=576.2] was treated with HCl in 1,4-dioxane (4M, 1.0 mL) at RT for 3 h. The solvent was evaporated. The residue was washed with ether and dried to give the desired product.

Workup

  1. washwashed with NaHCO3 (7.5%) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe residue [LCMS: (M+H)=576.2] was treated with HCl in 1,4-dioxane (4M, 1.0 mL) at RT for 3 h
  6. customThe solvent was evaporated
  7. washThe residue was washed with ether
  8. customdried

Sources & evidence

ORD record
ord-31c86b2fe4e44580ba26e36084e4ee1c
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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