Diisopropylethylamine → HCID 58116981, compound

HRID 38589Notes

Reaction equation

HRID 38589 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][NH:21][CH2:22][C:17]=4[O:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl.[CH3:24][N:25]([CH3:32])[CH2:26]/[CH:27]=[CH:28]/[C:29](O)=[O:30].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[C:18]4[CH2:19][CH2:20][N:21]([C:29](=[O:30])/[CH:28]=[CH:27]/[CH2:26][N:25]([CH3:32])[CH3:24])[CH2:22][C:17]=4[O:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45358758(2E)-4-(Dimethylamino)-2-butenoic acid hydrochlorideHCID 58116897N-(3-Chloro-4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4',3':4,5]furo[2,3-d]pyrimidin-4-amine

Product 1

HCID 58116981HCID 58116981, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of N-(3-chloro-4-fluorophenyl)-5,6,7,8-tetrahydropyrido[4′,3′:4,5]furo[2,3-d]pyrimidin-4-amine from Example 39A (100 mg, 0.314 mmol) and (2E)-4-(dimethylamino)but-2-enoic acid hydrochloride from Example 1A (73 mg, 0.44 mmol) in THF (2 mL) was treated with DIPEA (160 mg, 1.26 mmol) and TBTU (150 mg, 0.47 mmol). The mixture was stirred at rt overnight and then purified directly by preparative HPLC. The product crystallized upon trituration with diethyl ether to afford 76 mg (56%) of the title compound.

Workup

  1. custompurified directly by preparative HPLC
  2. customThe product crystallized upon trituration with diethyl ether

Sources & evidence

ORD record
ord-c12a4c1d4140464f89918f9c0ef9ddf9
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Reaction notes

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