Methylamine → HCID 56592092, compound

HRID 714480Notes

Reaction equation

HRID 714480 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][C@H:9]([C:11]2[CH:12]=[C:13]([C:17](O)=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=2)[C:3]=1[C:32]#[N:33].[CH3:34][N:35](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH:9]([C:11]2[CH:12]=[C:13]([C:17]([NH:35][CH3:34])=[O:18])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=2)[C:3]=1[C:32]#[N:33]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 56592009HCID 56592009, compound

Product 1

HCID 56592092HCID 56592092, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

33 mg (0.072 mmol) of rac-3-[(1S)-1-({6-amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]-pyridin-2yl}sulfanyl)ethyl]benzenecarboxylic acid (Example 16) were initially charged in 0.66 ml of DMF. At 0° C., 54.5 mg (0.143 mmol) of HATU were added, and the reaction solution was stirred at 0° C. for 20 min. After addition of 6.7 mg (0.215 mmol) of methylamine (2N in tetrahydrofuran) and 18.5 mg (0.143 mmol) of N,N-diisopropylethylamine, the mixture was stirred at RT overnight. The reaction solution was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. customThe reaction solution was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-c803adcd9ba448268742ceb9aea91d1e
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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