Sodium Hydroxide → HCID 86726869, compound

HRID 924387Notes

Reaction equation

HRID 924387 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:24](O)=[O:25])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:22]=[CH2:23])[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1[N:34]1[CH2:39][CH2:38][CH2:37][C@H:36]([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[OH-].[Na+]>CN(C=O)C>[C:43]([O:42][C:41]([NH:40][C@H:36]1[CH2:37][CH2:38][CH2:39][N:34]([C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:24]([C:13]2[C:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:21][C:20]3[C:15](=[CH:16][C:17]([CH:22]=[CH2:23])=[CH:18][CH:19]=3)[N:14]=2)=[O:25])[CH2:35]1)=[O:47])([CH3:44])([CH3:46])[CH3:45]

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59332360(S)-tert-Butyl (1-(3-aminopyridin-4-yl)piperidin-3-yl)carbamateHCID 867268683-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid

Product 1

HCID 86726869HCID 86726869, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-{[(Benzyloxy)carbonyl]amino}-7-vinylquinoline-2-carboxylic acid (0.55 g, 1.6 mmol) was mixed with tert-butyl [(3S)-1-(3-aminopyridin-4-yl)piperidin-3-yl]carbamate (0.46 g, 1.6 mmol), DMF (4.0 mL), HATU (1.2 g, 3.2 mmol) and DIPEA (1.1 mL, 6.3 mmol). The reaction mixture was stirred at room temperature for 16 h. Aq. NaOH (1 M, 20 mL) was then added to the reaction mixture. A precipitate formed, which was collected by vacuum filtration to give the sub-title compound (0.52 g, 53%) as light yellow powder. LCMS calc. for C35H39N6O5 (M+H)+: m/z=623.2. Found: 623.3.

Workup

  1. customA precipitate formed
  2. filtrationwhich was collected by vacuum filtration

Sources & evidence

ORD record
ord-142192a37df84dbe941220b9ae8d489c
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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