Isopropyl isocyanate → HCID 59375140, compound

HRID 1811160Notes

Reaction equation

HRID 1811160 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([C:27]5[N:28]([CH3:32])[CH:29]=[CH:30][N:31]=5)=[O:26])[C:19]=4[CH3:33])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.[N:34]([CH:37]([CH3:39])[CH3:38])=[C:35]=[O:36]>ClCCCl>[CH:37]([NH:34][C:35](=[O:36])[NH:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[C:7]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH:24][C:25]([C:27]5[N:28]([CH3:32])[CH:29]=[CH:30][N:31]=5)=[O:26])[C:19]=4[CH3:33])=[CH:8][CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1)([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanate2×HCID 66605948HCID 66605948, compound

Product 1

HCID 59375140HCID 59375140, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 7-amino-4-(2-methyl-3-(1-methyl-1H-imidazole-2-carboxamido)phenyl)-9H-carbazole-1-carboxamide (Example 54-15, 29 mg, 0.066 mmol) and 2-isocyanatopropane (0.019 mL, 0.198 mmol) in 1,2-dichloroethane (3 mL) was stirred at rt for 2.5 h, then at 50° C. for 2 h. Additional 2-isocyanatopropane was added and the mixture was stirred at 40° C. for 16 h. The mixture was concentrated and purified by HPLC. The appropriate effluent fractions were partially concentrated, treated with NaHCO3 (aq) and extracted with EtOAc. The organic phase was dried and concentrated to provide 7-(3-isopropylureido)-4-(2-methyl-3-(1-methyl-1H-imidazole-2-carboxamido)phenyl)-9H-carbazole-1-carboxamide as a pale pink solid (15 mg, 43%). 1H NMR (400 MHz, DMSO-d6) δ 11.32 (1 H, s), 9.97 (1 H, s), 8.37 (1 H, s), 8.13 (1 H, br. s.), 7.88 (1 H, d, J=7.9 Hz), 7.81 (1 H, d, J=1.8 Hz), 7.76 (1 H, d, J=7.9 Hz), 7.40-7.48 (2 H, m), 7.38 (1 H, t, J=7.7 Hz), 7.13 (1 H, d, J=7.5 Hz), 7.06 (1 H, s), 6.82-6.92 (2 H, m), 6.73 (1 H, d, J=8.3 Hz), 5.98 (1 H, d, J=7.5 Hz), 4.01 (3 H, s), 3.68-3.81 (1 H, m), 1.89-1.95 (3 H, m), 1.07 (6 H, d). Mass spectrum m/z 524.3 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by HPLC
  3. concentrationThe appropriate effluent fractions were partially concentrated
  4. additiontreated with NaHCO3 (aq)
  5. extractionextracted with EtOAc
  6. customThe organic phase was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d8ca0cb9c56c4b44a890d7a79207a045
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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