Diisopropylethylamine → HCID 58116944, compound

HRID 38627Notes

Reaction equation

HRID 38627 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]([C:24]#[N:25])=[CH:22][N:21]=[C:20]3[S:26][C:27]4[CH2:28][NH:29][CH2:30][CH2:31][C:32]=4[C:19]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1.Cl.[CH3:34][N:35]([CH:42]([CH3:44])[CH3:43])[CH2:36]/[CH:37]=[CH:38]/[C:39](O)=[O:40].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:17][C:18]2[C:23]([C:24]#[N:25])=[CH:22][N:21]=[C:20]3[S:26][C:27]4[CH2:28][N:29]([C:39](=[O:40])/[CH:38]=[CH:37]/[CH2:36][N:35]([CH3:34])[CH:42]([CH3:44])[CH3:43])[CH2:30][CH2:31][C:32]=4[C:19]=23)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58116874HCID 58116874, compoundHCID 86650197(2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride

Product 1

HCID 58116944HCID 58116944, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c′]dipyridine-3-carbonitrile from Example 90A (80 mg, 0.17 mmol) and (2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride from Example 2A (47 mg, 0.24 mmol) in DMF (2 mL) was treated with DIPEA (89 mg, 0.69 mmol) and TBTU (83 mg, 0.26 mmol). The mixture was stirred at rt overnight and then directly purified by preparative HPLC to yield 63 mg (61%) of the title compound.

Workup

  1. customdirectly purified by preparative HPLC

Sources & evidence

ORD record
ord-6d011b3d17f6494eb1b144b2b3b1382c
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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