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Diisopropylethylamine → 3-Hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

HRID 1055717
Notes
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Reaction equation

HRID 1055717 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([S:33]([F:38])([F:37])([F:36])([F:35])[F:34])[CH:32]=1)[C:27](O)=[O:28].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([S:33]([F:38])([F:34])([F:35])([F:36])[F:37])[CH:32]=1)[C:27]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

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 581367943-Hydroxy-5-(pentafluorosulfanyl)benzoic acidHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 89700329
3-Hydroxy-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pentafluoro-lambda6-sulphanyl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

300 mg (1.04 mmol) of the compound of Example 6A, 301 mg (1.14 mmol) of the compound of Example 24A and 473 mg (1.24 mmol) of HATU were initially charged in 3.6 ml of DMF, 0.36 ml (2.07 mmol) of N,N-diisopropylethylamine was added and the mixture was stirred at RT for two days. The reaction was then directly separated into its components by preparative HPLC (Method 18). This gave 180 mg (31% of theory) of the title compound.

Workup

  1. customThe reaction was then directly separated into its components by preparative HPLC (Method 18)

Sources & evidence

ORD record
ord-873263a4469f4703ad6afe5b899a3660
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394309B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes