Methylamine → HCID 57515840, compound

HRID 1921924Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:5]=[C:6]2[C@@H:11]([NH:12][CH2:13][C@H:14]([C@@H:16]([NH:20][C:21](=[O:23])[CH3:22])[CH2:17][CH:18]=[CH2:19])[OH:15])[CH2:10][C:9]3([CH2:26][CH2:25][CH2:24]3)[O:8][C:7]=12.[CH3:32][N:33](C1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=CC=1)C.CN.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[CH3:29][C:28]([CH3:31])([CH3:30])[CH2:27][C:4]1[CH:5]=[C:6]2[C@@H:11]([NH:12][CH2:13][C@H:14]([C@@H:16]([NH:20][C:21](=[O:23])[CH3:22])[CH2:17][CH:18]=[CH2:19])[OH:15])[CH2:10][C:9]3([CH2:26][CH2:25][CH2:24]3)[O:8][C:7]2=[C:2]([NH:33][CH3:32])[N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a flame-dried microwave vial under Ar gas was added N-((1S)-1-((1R)-2-(((4′S)-8′-chloro-6′-(2,2-dimethylpropyl)-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-c]pyridin]-4′-yl)amino)-1-hydroxyethyl)-3-buten-1-yl)acetamide (120 mg, 267 μmol), Pd2 dba3 (49 mg, 53 μmol), and DavePhos (46 mg, 117 μmol). The vial was purged with N2 5×, then THF (3 mL), methanamine (533 μl, 1067 μmol), and LiHMDS (2400 μl, 2400 μmol) were added. The vial was sealed and heated in a microwave at 110° C. for 10 min. The reaction mixture was directly purified by reverse phase HPLC to give the title compound as an amorphous white solid. MS m/z: 445.3 (M+1).

Workup

customThe vial was purged with N2 5×
customThe vial was sealed
customThe reaction mixture was directly purified by reverse phase HPLC

Sources & evidence

ORD record: ord-ec510cd9cd4a4dd19800d7e88b089469
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173810B2

Reaction notes

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