Triethylamine → HCID 86592548, compound

HRID 1432987Notes

Reaction equation

HRID 1432987 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@H:17]([CH3:19])[NH:16][C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)CC)C.[Cl:51][C:52]1[S:56][C:55]([CH:57]=[CH:58][C:59](O)=[O:60])=[CH:54][CH:53]=1>CN(C=O)C>[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][N:13]3[CH2:18][C@H:17]([CH3:19])[N:16]([C:59](=[O:60])[CH:58]=[CH:57][C:55]4[S:56][C:52]([Cl:51])=[CH:53][CH:54]=4)[C@@H:15]([CH3:20])[C:14]3=[O:21])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 534018273-(5-Chlorothiophen-2-yl)prop-2-enoic acidHCID 57197935HCID 57197935, compound

Product 1

HCID 86592548HCID 86592548, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S,5S)-1-(4-amino-quinazolin-7-ylmethyl)-3,5-dimethyl-piperazin-2-one (42 mg, 0.147 mmol), major epimer from EXAMPLE 88, Part D, in 2 mL of DMF is added TBTU (52 mg, 0.162 mmol), triethylamine (0.02 mL, 0.162 mmol) and 3-(5-chloro-thiophen-2-yl)-acrylic acid (28 mg, 0.15 mmol), EXAMPLE 25. After stirring for two hours, the reaction mixture is directly purified by reverse phase HPLC (10-70% ACN/H2O). The product (35.5 mg, 36%) is isolated as a yellow solid with a melting point of 116-120° C. C22H22ClN5O2S: MS m/z: 456, 458. Anal. calcd. for C22H22ClN5O2S.C2HF3O2: C, 50.57; H, 4.07; N, 12.29. Found: C, 46.48; H, 3.64; N, 11.04.

Workup

  1. customthe reaction mixture is directly purified by reverse phase HPLC (10-70% ACN/H2O)

Sources & evidence

ORD record
ord-21e06d9702ce45709c67532407f4862d
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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