Sodium Methoxide → HCID 178521000, compound

HRID 931329Notes

Reaction equation

C[O-].[Na+].[NH2:4][C:5]1[C:10]([NH:11][C:12]([C:14]2([C:17]3[N:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH2:16][CH2:15]2)=O)=[CH:9][CH:8]=[C:7]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH2:24]2)[N:6]=1>C(O)C(C)C.CO>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]2([C:12]3[NH:4][C:5]4=[N:6][C:7]([N:23]5[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:31]6[CH2:35][CH2:34][CH2:33][CH2:32]6)=[O:30])[CH2:24]5)=[CH:8][CH:9]=[C:10]4[N:11]=3)[CH2:16][CH2:15]2)[N:18]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Sodium methoxide (74.4 mg, 1.37 mmol) was added to a solution of (R)—N-(2-amino-6-(3-(pyrrolidine-1-carbonyl)piperidin-1-yl)pyridin-3-yl)-1-(pyridazin-3-yl)cyclopropanecarboxamide (100 mg, 0.22 mmol) in isobutanol (2 mL) and methanol (2 mL). The reaction mixture was heated to 110° C. for 16 h. The reaction mixture was concentrated under reduced pressure and the resulting crude was purified via preparative TLC to afford the title compound (35 mg). MS (ES+APCI) (M+H) 418.2; LCMS retention time: 3.439 min (Method W1).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting crude was purified via preparative TLC

Sources & evidence

ORD record: ord-0bb98076d8b840fcacc0c329fc790b5c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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