Dimethylformamide → HCID 22057962, compound

HRID 2302273Notes

Reaction equation

HRID 2302273 reaction equation
C(N(C(C)C)CC)(C)C.O1C[CH2:14][N:13]([C:16]2[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=2)[C:19]([OH:21])=O)[CH2:12]C1.[NH2:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:45])=[C:30]([NH:32][C:33]([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][CH:39]=[CH:38]3)=[O:34])[CH:31]=1.CN(C=O)C>O>[CH3:14][N:13]([CH3:12])[C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([CH3:45])=[C:30]([NH:32][C:33]([C:35]2[CH:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][CH:39]=[CH:38]3)=[O:34])[CH:31]=1)=[O:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27955493-(Morpholin-4-yl)benzoic acidHCID 22057974HCID 22057974, compound

Product 1

HCID 22057962HCID 22057962, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diisopropylethylamine (0.174 ml) was added to a stirred mixture of 3-morpholinobenzoic acid (0.104 g), N-(5-amino-2-methylphenyl)quinoline-6carboxamide (0.14 g), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.23 g) and DMF (1 ml) and the resultant mixture was stirred at ambient temperature for 16 hours. The reaction mixture was poured into water and the resultant solid was isolated, washed with a saturated aqueous sodium bicarbonate solution and dried in a vacuum oven. There was thus obtained the title compound (0.216 g); NMR Spectrum: (DMSOd6) 2.25 (s, 3H), 3.18 (m, 4H), 3.75 (m, 4H), 7.14 (d, 1H), 7.25 (d, 1H), 7.36 (m, 2H), 7.44 (s, 1H), 7.62 (m, 2H), 7.86 (s, 1H), 8.13 (d, 1H), 8.28 (d, 1H), 8.52 (d, 1H), 8.65 (s, 1H), 9.0 (s, 1H), 10.14 (m, 2H); Mass Spectrum: M+H+ 467.

Workup

  1. customthe resultant solid was isolated
  2. washwashed with a saturated aqueous sodium bicarbonate solution
  3. customdried in a vacuum oven

Sources & evidence

ORD record
ord-7132d434fe2942dd970b509f3f1cf6dc
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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