Diisopropylethylamine → HCID 22353378, compound

HRID 1783341Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:30])[CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[CH:3]=1.C(N(CC)C(C)C)(C)C.Cl.[NH2:41][CH2:42][C:43]([NH2:45])=[O:44]>>[NH2:45][C:43](=[O:44])[CH2:42][NH:41][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][C:15](=[O:30])[CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)[CH:3]=1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 2723639Glycinamide hydrochloride

HCID 22379064HCID 22379064, compound

Product 1

HCID 22353378HCID 22353378, compoundYield 39.9%

Conditions

Temperature: 100 °C

Procedure

To a crude sample of N-(6-chloro-2-phenylpyrimidin-4-yl)-2-(4-benzylpiperidin-1-yl)acetamide (22.55) (0.75 g in 60 ml DMSO) were added glycinamide hydrochloride (1.85 g in 10 ml DMSO) and N,N-diisopropylethylamine (2.96 ml) and the mixture heated to 100° C. for 16 hrs. The solvent was then removed in vacuo and the residue purified by flash chromatography on silica gel using mixtures of dichloromethane and methanol (97:3, 95:5 then 93:7 v/v/v). Further purification by recrystallization from methanol furnished the title compound (326 mg over 2 steps).

Workup

customThe solvent was then removed in vacuo
customthe residue purified by flash chromatography on silica gel using mixtures of dichloromethane and methanol (97:3, 95:5
customFurther purification
customby recrystallization from methanol

Sources & evidence

ORD record: ord-0a0a39dd53a4470291acef8ebdbb327d
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501407B2

Reaction notes

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