Methanol → HCID 178521002, compound

HRID 931293Notes

Reaction equation

[NH2:1][C:2]1[C:7]([NH:8][C:9]([C:11]2([C:14]3[CH:19]=[N:18][CH:17]=[CH:16][N:15]=3)[CH2:13][CH2:12]2)=O)=[CH:6][CH:5]=[C:4]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:27])[CH2:21]2)[N:3]=1.CO.C[O-].[Na+]>C(O)C(C)C>[N:15]1[CH:16]=[CH:17][N:18]=[CH:19][C:14]=1[C:11]1([C:9]2[NH:1][C:2]3=[N:3][C:4]([N:20]4[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([N:28]5[CH2:32][CH2:31][CH2:30][CH2:29]5)=[O:27])[CH2:21]4)=[CH:5][CH:6]=[C:7]3[N:8]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-1-(pyrazin-2-yl)cyclopropanecarboxamide (0.1 g, 0.22 mmol) in anhydrous methanol (0.072 mL, 1.78 mmol) was added sodium methoxide (54 mg, 1.1 mmol) and isobutanol (3.5 mL). The reaction mixture was heated at 100° C. for 18 h. The solvent was removed under reduced pressure and the crude material was purified via preparative TLC to afford the title compound (19 mg). MS (ES+APCI) (M+H) 418.1; LCMS retention time 4.792 min (Method R1).

Workup

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

Sources & evidence

ORD record: ord-15fe885cdafb4c3b8b422ddcbe7ce2ad
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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