Diisopropylethylamine → HCID 59415860, compound

HRID 2061813Notes

Reaction equation

HRID 2061813 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][C:21]([NH:33][C:34]([NH:36][CH2:37][CH3:38])=[O:35])=[CH:22][C:23]=3[C:24]3[S:25][CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=3)=[CH:15][CH:16]=2)[C:11](=[O:39])[C:10]([C:40](O)=[O:41])=[CH:9]1)[CH2:5][O:6][CH3:7].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.[NH2:77][CH:78]1[CH2:83][CH2:82][O:81][CH2:80][CH2:79]1>CN(C=O)C.O>[CH3:7][O:6][CH2:5][CH:4]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][C:21]([NH:33][C:34]([NH:36][CH2:37][CH3:38])=[O:35])=[CH:22][C:23]=3[C:24]3[S:25][CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[N:28]=3)=[CH:15][CH:16]=2)[C:11](=[O:39])[C:10]([C:40]([NH:77][CH:78]2[CH2:83][CH2:82][O:81][CH2:80][CH2:79]2)=[O:41])=[CH:9]1)[CH2:3][O:2][CH3:1]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441186934-Aminotetrahydropyran hydrochlorideHCID 59415803HCID 59415803, compound

Product 1

HCID 59415860HCID 59415860, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(1,3-Dimethoxypropan-2-yl)-6-(6-(3-ethylureido)-4-(4-(trifluoromethyl)thiazol-2-yl)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (Example 4, 0.112 g, 0.18 mmol) was suspended in DMF (1 mL). O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (0.105 g, 0.28 mmol) was added, followed by diisopropylethylamine (0.193 mL, 1.11 mmol). The reaction mixture was stirred for 15 min at RT. The 4-aminotetrahydropyran hydrochloride (0.038 g, 0.28 mmol) was added in one portion and the mixture was stirred at RT for 2 days. Water was added and the resultant solid was purified by column chromatography (silica, 95:5 methylene chloride/methanol) to provide the product as a solid. The solid was further purified by trituration with CH2Cl2 and hexanes.

Workup

  1. stirringthe mixture was stirred at RT for 2 days
  2. customthe resultant solid was purified by column chromatography (silica, 95:5 methylene chloride/methanol)

Sources & evidence

ORD record
ord-329b10059b3f4adfb6b514d6f71b5ecc
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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