Benzoic Acid → HCID 22378841, compound

HRID 895495Notes

Reaction equation

HRID 895495 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:43][CH2:44][CH2:45][NH:46][C:47]1[N:52]=[C:51]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[N:50]=[C:49]([NH:59][CH2:60][CH2:61][NH:62][C:63](=[O:65])[CH3:64])[C:48]=1[CH3:66]>CN1C(=O)CCC1>[C:63]([NH:62][CH2:61][CH2:60][NH:59][C:49]1[N:50]=[C:51]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[N:52]=[C:47]([NH:46][CH2:45][CH2:44][NH:43][C:1](=[O:9])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:48]=1[CH3:66])(=[O:65])[CH3:64]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22353380HCID 22353380, compound

Product 1

HCID 22378841HCID 22378841, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Benzoic acid (55.8 mg), N,N-diisopropylethylamine (80 μl) and HATU (160 mg) were stirred in NMP (6851 μl) for 30 min. After this time N-[2-({6-[(2-aminoethyl)amino]-5-methyl-2-phenylpyrimidin-4-yl}amino)ethyl]acetamide (150 mg) was added and the mixture stirred for 16 hrs at room temperature. Purification via SCX resin furnished the title compound (54 mg).

Workup

  1. customPurification via SCX resin

Sources & evidence

ORD record
ord-916a46874d694980ae5ad380d44c4d38
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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