Phenylacetic Acid → HCID 59704975, compound

HRID 605869Notes

Reaction equation

HRID 605869 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][CH:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)[C:13]([NH2:23])=[CH:12][N:11]=3)[C:6]=2[CH:24]=1.[C:25]1([CH2:31][C:32](O)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.Cl.CN(C)CCCN=C=NCC>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14]([NH:16][CH:17]4[CH2:18][CH2:19][O:20][CH2:21][CH2:22]4)[C:13]([NH:23][C:32](=[O:33])[CH2:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:12][N:11]=3)[C:6]=2[CH:24]=1

Participants

5

Reactant 3

HCID 999Phenylacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59704965HCID 59704965, compound

Product 1

HCID 59704975HCID 59704975, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of 10 mg (0.030 mmol) 2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-N4-(tetrahydro-2H-pyran-4-yl) pyrimidine-4,5-diamine in 1 mL acetonitrile was added 16 mg (0.12 mmol) of phenylacetic acid and 20 mg (excess) 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride. The solution was stirred for 1 hr at room temperature. Solvent was removed under vacuum and column chromatography with 5% MeOH in DCM provided 10 mg (75%) pale yellow solid as the desired amide.

Workup

  1. customSolvent was removed under vacuum and column chromatography with 5% MeOH in DCM

Sources & evidence

ORD record
ord-bba532b8269d43fdae06c9b00819fdd6
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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