Acetic Acid → HCID 178521003, compound

HRID 931295Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1([CH:10]=O)[CH2:9][CH2:8]1.[S].C(O)(=O)C.[NH2:17][C:18]1[CH:19]=[CH:20][C:21]([N:25]2[CH2:30][CH2:29][CH2:28][C@@H:27]([C:31]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)=[O:32])[CH2:26]2)=[N:22][C:23]=1[NH2:24]>C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:1][C:2]=1[C:7]1([C:10]2[NH:24][C:23]3=[N:22][C:21]([N:25]4[CH2:30][CH2:29][CH2:28][C@@H:27]([C:31]([N:33]5[CH2:37][CH2:36][CH2:35][CH2:34]5)=[O:32])[CH2:26]4)=[CH:20][CH:19]=[C:18]3[N:17]=2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(Pyrimidin-2-yl)cyclopropanecarbaldehyde (0.11 g, 0.747 mmol), sulfur (40 mg, 1.24 mmol), and acetic acid (0.6 mL) were added to a solution of (R)-(1-(5,6-diaminopyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone, prepared during the previous step, in ethanol. The reaction mixture was heated to 80° C. for 18 h. The solvent was removed under reduced pressure and the crude material was purified via preparative HPLC to afford the title compound (8 mg). MS (ES+APCI) (M+H) 418.2; LCMS retention time 3.273 min (Method S1).

Workup

customThe solvent was removed under reduced pressure
customthe crude material was purified via preparative HPLC

Sources & evidence

ORD record: ord-01d9ae7ed6cc4d74b2653719ce9b73f5
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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