1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-((4-bromo-2-chlorophenyl)amino)-N-((2,2-dimethyl-1, 3-dioxolan-4-yl)methoxy)-4-fluorobenzo[d]oxazole-6-carboxamide

HRID 928974Notes

Reaction equation

HRID 928974 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19]([OH:21])=O)=[CH:11][C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:22])[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:44][C:45]1([CH3:53])[O:49][CH:48]([CH2:50][O:51][NH2:52])[CH2:47][O:46]1.[NH4+].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([C:19]([NH:52][O:51][CH2:50][CH:48]3[CH2:47][O:46][C:45]([CH3:53])([CH3:44])[O:49]3)=[O:21])=[CH:11][C:12]3[O:16][CH:15]=[N:14][C:13]=3[C:17]=2[F:18])=[C:4]([Cl:22])[CH:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 10240948O-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]hydroxylamineHCID 897048215-((4-Bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid

Product 1

HCID 897050365-((4-bromo-2-chlorophenyl)amino)-N-((2,2-dimethyl-1, 3-dioxolan-4-yl)methoxy)-4-fluorobenzo[d]oxazole-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-((4-bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]oxazole-6-carboxylic acid (463 mg, 1.20 mmol) in CH2Cl2 (10 mL) was added HOBt (254 mg, 1.63 mmol) followed by EDCI (314 mg, 1.63 mmol). The mixture was stirred for 1 h and O-((2,2-dimethyl-1,3-di-oxolan-4-yl)methyl)hydroxylamine (238 mg, 1.62 mmol) was added. After stirring for 4 h at ambient temperature, the reaction was treated with saturated NH4Cl (aq.). The resultant mixture was extracted with CH2Cl2 (30 mL×3). The combined organic extracts was washed by water (30 mL) and brine (30 mL) sequentially, dried over Na2SO4, filtered and concentrated in vacuo. The crude product (473 mg) was used directly in the next step without further purification.

Workup

  1. stirringAfter stirring for 4 h at ambient temperature
  2. extractionThe resultant mixture was extracted with CH2Cl2 (30 mL×3)
  3. washThe combined organic extracts was washed by water (30 mL) and brine (30 mL) sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product (473 mg) was used directly in the next step without further purification

Sources & evidence

ORD record
ord-444ea768741b420d9027adc160cfa97d
Source dataset
uspto-grants-2016_03
Patent number
US09290468B2

Reaction notes

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