1-Hydroxybenzotriazole → HCID 59627695, compound

HRID 1930155Notes

Reaction equation

HRID 1930155 reaction equation
CC(NC)(C)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH2:16]([N:18]([CH:22](C)C)[CH:19]([CH3:21])[CH3:20])C.[C:25]([C:28]1[N:33]=[C:32]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([CH2:46]C(O)=O)=[CH:42][C:41]=3[Cl:50])=[CH:36][CH:35]=2)[C:31]([CH3:51])=[N:30][C:29]=1[CH3:52])(=[O:27])[NH2:26].Cl.CN(C)CCCN=C=NCC.N1([OH:74])C2C=CC=CC=2N=N1>CN(C=O)C>[C:25]([C:28]1[N:33]=[C:32]([C:34]2[CH:35]=[CH:36][C:37]([C:40]3[CH:45]=[CH:44][C:43]([CH2:46][C:16]([N:18]([C:19]([CH3:20])([CH3:21])[C:3]([O:5][CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[O:4])[CH3:22])=[O:74])=[CH:42][C:41]=3[Cl:50])=[CH:38][CH:39]=2)[C:31]([CH3:51])=[N:30][C:29]=1[CH3:52])(=[O:27])[NH2:26]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498471732-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acidHCID 62820700HCID 62820700, compound

Product 1

HCID 59627695HCID 59627695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of benzyl 2-methyl-2-(methylamino)propanoate (118 mg, 0.57 mmol) and N-ethyl-N-isopropylpropan-2-amine (99 μL, 0.57 mmol) in DMF (342 μL) were treated with a solution of 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid (Example 1; 205 mg, 0.52 mmol), 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (124 mg, 0.65 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (70.0 mg, 0.52 mmol) and N-ethyl-N-isopropylpropan-2-amine (99 μL, 0.57 mmol) in DMF (2049 μL) at RT. The resulting solution was stirred at RT for 20 hours. The reaction mixture was evaporated to dryness and redissolved in DCM (5 mL), and washed with water (5 mL). The organic layer was evaporated to afford crude product which was used without further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in DCM (5 mL)
  3. washwashed with water (5 mL)
  4. customThe organic layer was evaporated
  5. customto afford crude product which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-630b6d69341441c79c892edc01e64c7c
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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