Water → HCID 178496648, compound

HRID 1486930Notes

Reaction equation

HRID 1486930 reaction equation
C([N:3]([CH2:6]C)CC)C.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][C:13](C(O)=O)=[C:12]2[NH:22][C@H:23]1[CH2:26][C@@H:25]([O:27][CH3:28])[CH2:24]1.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:30]C1C=CC=CC=1.O>CN(C=O)C>[Br:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[CH:14][C:13]3[NH:3][C:6](=[O:30])[N:22]([C@H:23]4[CH2:24][C@@H:25]([O:27][CH3:28])[CH2:26]4)[C:12]=3[C:11]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 178496654HCID 178496654, compound

Product 1

HCID 178496648HCID 178496648, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Triethylamine (39.3 mL, 281.89 mmol) was added to 6-bromo-4-[(cis-3-methoxycyclobutyl)amino]quinoline-3-carboxylic acid (33 g, 93.96 mmol) in DMF (200 mL) at r.t. After stirring for 30 minutes diphenyl phosphorazidate (28.4 g, 103.36 mmol) was added and the resulting mixture stirred at 60° C. for 2 h. The reaction mixture was poured into water (500 mL), the precipitate collected by filtration, washed with water (200 mL) and dried under vacuum to afford the desired material (32.0 g, 98%) as a yellow solid, which was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 2.75-2.82 (2H, m), 2.9-3.05 (2H, m), 3.22 (3H, s), 3.80-3.90 (1H, m), 4.85-4.99 (1H, m), 7.71 (1H, dd), 7.94 (1H, d), 8.48 (1H, d), 8.69 (1H, s), 10.42 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=348, 350.

Workup

  1. additionwas added
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water (200 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-28b733e28ad04ac5879c135fdd9b8394
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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