Morpholin-4-ylmalononitrile → 2-[1-(2-Fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazol-3-yl]-5-(morpholin-4-yl)pyrimidine-4,6-diamine

HRID 1482925Notes

Reaction equation

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

Participants

Conditions

Temperature: 105 °C

Procedure

75 mg of 1-(2-fluorobenzyl)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboximidamide 1-2-4 (0.29 mmol, 1.0 eq.) and 44 mg morpholin-4-ylmalononitrile [0.29 mmol, 1.0 eq.; for preparation see: H. Gold and O. Bayer, Chem. Ber. 94, 2594 (1961)] were suspended in a small amount of DCM and the resulting suspension was evaporated to dryness. The residue was heated for one h at 105° C. The crude product was purified by flash chromatography yielding 86 mg (0.21 mmol, 72%) of analytically pure target compound.

Workup

customfor preparation
customthe resulting suspension was evaporated to dryness
customThe crude product was purified by flash chromatography
customyielding 86 mg (0.21 mmol, 72%) of analytically pure target compound

Sources & evidence

ORD record: ord-663f5e82f3074c0e979d5eca389876bd
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416125B2

Reaction notes

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