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1-Hydroxybenzotriazole → Methyl 2-(2-(4'-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)acetate

HRID 1930159
Notes
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Reaction equation

HRID 1930159 reaction equation
[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][C:17]=3[Cl:26])=[CH:12][CH:11]=2)[C:7]([CH3:27])=[N:6][C:5]=1[CH3:28])(=[O:3])[NH2:2].Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.Cl.[NH2:61][CH2:62][C:63]([O:65][CH3:66])=[O:64]>CN(C=O)C>[C:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][C:23]([NH:61][CH2:62][C:63]([O:65][CH3:66])=[O:64])=[O:24])=[CH:18][C:17]=3[Cl:26])=[CH:12][CH:11]=2)[C:7]([CH3:27])=[N:6][C:5]=1[CH3:28])(=[O:3])[NH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester 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 67285289
Methyl 2-(2-(4'-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)acetate
Yield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetic acid (Example 1; 250 mg, 0.63 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (151 mg, 0.79 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (85 mg, 0.63 mmol) and N-ethyl-N-isopropylpropan-2-amine (242 μL, 1.39 mmol) in DMF (2499 μL) was treated with a solution of methyl 2-aminoacetate hydrochloride (87 mg, 0.69 mmol) in DMF (417 μL) at 23° C. The resulting solution was stirred at RT for 4 hours. The reaction mixture was evaporated to dryness and redissolved in EtOAc (25 mL), and washed sequentially with saturated brine (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford methyl 2-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetamido)acetate (266 mg, 90%) which was used without further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in EtOAc (25 mL)
  3. washwashed sequentially with saturated brine (50 mL) and water (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-33db9c1a1e1546fe9514de9c099af28a
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188092B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes