Diisopropylethylamine → HCID 58116988, compound

HRID 38611

Reaction equation

HRID 38611 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][C:11]2[C:12]3[C:19]4[CH2:20][CH2:21][NH:22][CH2:23][C:18]=4[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][C:4]=1[OH:24].Cl.[CH3:26][N:27]([CH:34]([CH3:36])[CH3:35])[CH2:28]/[CH:29]=[CH:30]/[C:31](O)=[O:32].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:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([NH:10][C:11]2[C:12]3[C:19]4[CH2:20][CH2:21][N:22]([C:31](=[O:32])/[CH:30]=[CH:29]/[CH2:28][N:27]([CH3:26])[CH:34]([CH3:36])[CH3:35])[CH2:23][C:18]=4[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[CH:5][C:4]=1[OH:24]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 668498872,3-Dichloro-5-(5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochlorideHCID 86650197(2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride

Product 1

HCID 58116988HCID 58116988, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dichloro-5-(5,6,7,8-tetrahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrimidin-4-ylamino)phenol hydrochloride from Example 69A (51 mg, 0.13 mmol) and (2E)-4-[methyl(1-methylethyl)amino]but-2-enoic acid hydrochloride from Example 2A (34 mg, 0.18 mmol) were dissolved in DMF (1.5 mL), and DIPEA (82 mg, 0.63 mmol) and TBTU (61 mg, 0.19 mmol) were added. The mixture was stirred at rt overnight. The product was then directly isolated by preparative HPLC to yield 33 mg (52%) of the title compound.

Workup

  1. customThe product was then directly isolated by preparative HPLC

Sources & evidence

ORD record
ord-98645de9a8544ce6a55f6f788ac6ebd6
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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