N,N'-Dimethylethylenediamine → HCID 86707423, compound

HRID 338868Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[N:16]4[CH:17]=[C:18]([CH:21]([N:26]5[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27]5)[C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:20][C:15]4=[N:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:39]([NH2:44])(=[O:43])[CH:40]([CH3:42])[CH3:41].[O-]P([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1>[F:24][C:22]([F:23])([F:25])[CH:21]([N:26]1[CH2:30][CH2:29][C@H:28]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:27]1)[C:18]1[CH:19]=[CH:20][C:15]2[N:16]([C:12]([C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][C:2]([NH:44][C:39](=[O:43])[CH:40]([CH3:42])[CH3:41])=[CH:3][CH:4]=4)[N:9]=3)=[N:13][N:14]=2)[CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

tert-Butyl (3S)-1-(1-(3-(7-bromo quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (50 mg, 0.085 mmol), isobutyramide (18.4 mg, 0.211 mmol), K3PO4 (53.8 mg, 0.254 mmol), and Cu(I)I (1.61 mg, 0.0085 mmol) were weighed into a 40 mL Teflon® capped vial. The vial was purged with N2, followed by addition of toluene (20 mL) and N1,N2-dimethylethane-1,2-diamine (4.55 μL, 0.042 mmol). The reaction was sealed and heated to 90° C. overnight, after which the reaction complete by TLC. The crude reaction was concentrated, then purified by flash column chromatography (eluting with 10% MeOH/DCM), affording the desired product (55 mg, 97% yield).

Workup

customcapped vial
customThe vial was purged with N2
customThe reaction was sealed
customafter which the reaction complete by TLC
customThe crude reaction
concentrationwas concentrated
custompurified by flash column chromatography (eluting with 10% MeOH/DCM)

Sources & evidence

ORD record: ord-8486f0feca274257a8de731281d58ef9
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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