Triethylamine → HCID 72203100, compound

HRID 1482938Notes

Reaction equation

[F:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][N:5]1[C:9]2[CH2:10][CH2:11][CH2:12][C:8]=2[C:7]([C:13]2[N:18]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)[C:16]([O:26][CH3:27])=[C:15]([NH2:28])[N:14]=2)=[N:6]1.C(N(CC)CC)C.[CH3:40][O:41][CH2:42][C:43](Cl)=[O:44]>CN(C=O)C>[NH2:28][C:15]1[N:14]=[C:13]([C:7]2[C:8]3[CH2:12][CH2:11][CH2:10][C:9]=3[N:5]([CH2:4][C:3]3[CH:29]=[CH:30][CH:31]=[CH:32][C:2]=3[F:1])[N:6]=2)[N:18]=[C:17]([N:19]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[C:43](=[O:44])[CH2:42][O:41][CH3:40])[C:16]=1[O:26][CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

50 mg of 2-[1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4,6-diamine 2-1-4 (0.116 mmol, 1.0 eq.) and 12 mg of triethyl amine (0.116 mmol, 1.0 eq.) were dissolved in 600 μL DMF and were cooled to 0° C. After addition of 13 mg of methoxyacetyl chloride (0.116 mmol, 1.0 eq.), the reaction mixture was stirred for five h at rt. After dilution with water, the crude product was extracted with ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography yielding 37 mg (0.07 mmol, 60%) of analytically pure target compound.

Workup

extractionAfter dilution with water, the crude product was extracted with ethyl acetate
washThe combined organic layers were washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography
customyielding 37 mg (0.07 mmol, 60%) of analytically pure target compound

Sources & evidence

ORD record: ord-1841484692064423af25a3aa0a5e5dc2
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416125B2

Reaction notes

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