Hydrochloric Acid → HCID 86633089, compound

HRID 415239Notes

Reaction equation

HRID 415239 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([O-:20])=O)=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.C1C=CC2N(O)N=[N:27]C=2C=1.[NH4+].[Cl-].CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[C:17]([C:18]([NH2:27])=[O:20])=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86633090HCID 86633090, compound

Product 1

HCID 86633089HCID 86633089, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 2-(4-methoxyphenylbenzo[d]oxazole-7-carboxylate in DMF (15 mL) was added HOBt (148 mg, 1.1 mmol), NH4Cl (54 mg, 1.0 mmol), DIPEA (387 mg, 3.0 mmol) and EDCI (211 mg, 1.1 mmol). The mixture was stirred at 25° C. for 10 hr. To the resulting mixture, water (10 mL) and aqueous hydrochloric acid (1 N) were added to pH=3, then extracted with ethyl acetate (100 mL×4). The organic phase was washed with saturated sodium bicarbonate solution and brine, concentrated, and dried in vacuum. The crude product was purified by pre-HPLC to obtain 2-(4-methoxyphenylbenzo[d]oxazole-7-carboxamide as a white solid (8 mg, yield 3% for 2 steps). 1H-NMR (400 MHz, CDCl3-d) δ 3.93 (s, 3H), 6.16 (s, 1H), 7.06-7.08 (d, J=8 Hz, 3H), 7.47 (s, 1H), 7.90-8.18 (m, 4H); LC-MS (ESI) m/z 269 [M+1]+.

Workup

  1. extractionextracted with ethyl acetate (100 mL×4)
  2. washThe organic phase was washed with saturated sodium bicarbonate solution and brine
  3. concentrationconcentrated
  4. customdried in vacuum
  5. customThe crude product was purified by pre-HPLC

Sources & evidence

ORD record
ord-c828d6b7b0d049cf82e5ab5c52215922
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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