1-Hydroxybenzotriazole → HCID 59627652, compound

HRID 1930154Notes

Reaction equation

HRID 1930154 reaction equation
Cl.[NH2:2][C@@H:3]([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5].C(N(C(C)C)C(C)C)C.[C:20]([C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][C:42](O)=[O:43])=[CH:37][C:36]=3[Cl:45])=[CH:31][CH:30]=2)[C:26]([CH3:46])=[N:25][C:24]=1[CH3:47])(=[O:22])[NH2:21].Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1>CN(C=O)C>[C:20]([C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][C:38]([CH2:41][C:42]([NH:2][C@@H:3]([CH:8]([CH3:10])[CH3:9])[C:4]([O:6][CH3:7])=[O:5])=[O:43])=[CH:37][C:36]=3[Cl:45])=[CH:31][CH:30]=2)[C:26]([CH3:46])=[N:25][C:24]=1[CH3:47])(=[O:22])[NH2:21]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 111190Methyl valinate hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 498471732-(4'-(6-Carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid

Product 1

HCID 59627652HCID 59627652, compoundYield 124%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of (S)-methyl 2-amino-3-methylbutanoate hydrochloride (95 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 (S)-methyl 2-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)-3-methylbutanoate (327 mg, 124%) 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

Sources & evidence

ORD record
ord-a7a96e9fdf0947c386f3641d58f24884
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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