Methylamine → HCID 59415949, compound

HRID 2061814Notes

Reaction equation

HRID 2061814 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]([OH:42])=O)=[CH:9]1)[CH2:5][O:6][CH3:7].F[P-](F)(F)(F)(F)F.[N:50]1(OC(N(C)C)=[N+](C)C)[C:54]2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN.C1COCC1>CN(C=O)C.O>[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]([NH:50][CH3:54])=[O:42])=[CH:9]1)[CH2:5][O:6][CH3:7]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59415803HCID 59415803, compound

Product 1

HCID 59415949HCID 59415949, 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 (0.097 mL, 0.55 mmol). The reaction mixture was stirred for 15 min at RT. A 2.0 M solution of methylamine in THF (0.2 mL, 0.40 mmol) was added and the mixture was stirred at RT for 2 d. Water was added and the solid precipitate was purified by column chromatography (silica, 95:5 methylene chloride/methanol). The solid was further purified by trituration with CH2Cl2 and hexanes.

Workup

  1. stirringthe mixture was stirred at RT for 2 d
  2. customthe solid precipitate was purified by column chromatography (silica, 95:5 methylene chloride/methanol)
  3. customThe solid was further purified by trituration with CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-4a94f85fd39346faa18fd76cd71035a6
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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