Diisopropylethylamine → HCID 178495256, compound

HRID 1530679Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][CH:20]=1)[C:17]1[N:13]([CH:14]=[C:15]([C:21]3[N:25]([CH2:26][CH:27]([O:29][CH3:30])[CH3:28])[N:24]=[CH:23][N:22]=3)[N:16]=1)[CH2:12][CH2:11][O:10]2)=O.[NH:32]([CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1)[NH2:33].CCN(C(C)C)C(C)C>C(O)C>[C:43]([O:42]1[CH2:36][CH2:35][CH:34]([N:32]2[C:5]([C:7]3[CH:8]=[C:9]4[C:18](=[CH:19][CH:20]=3)[C:17]3[N:13]([CH:14]=[C:15]([C:21]5[N:25]([CH2:26][CH:27]([O:29][CH3:30])[CH3:28])[N:24]=[CH:23][N:22]=5)[N:16]=3)[CH2:12][CH2:11][O:10]4)=[CH:4][CH:3]=[N:33]2)[CH2:39][CH2:38][NH:37][C:40]1=[O:41])([CH3:46])([CH3:45])[CH3:44]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of (2E)-3-(dimethylamino)-1-{4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}prop-2-en-1-one (105 mg, 0.250 mmol), tert-butyl 4-hydrazinylpiperidine-1-carboxylate (108 mg, 0.500 mmol), and DIPEA (60 mg, 0.50 mmol) in ethanol (10 mL) was stirred at 80° C. for 48 h under nitrogen atmosphere. After concentration, the residue was purified by reverse phase Combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to give 1-tert-butyl-6-(5-{4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}-1H-pyrazol-1-yl)-1λ3,3-oxazocan-2-one (105 mg, 67% yield). LCMS (ESI) m/z: 422.1 [M+H+].

Workup

concentrationAfter concentration
customthe residue was purified by reverse phase Combiflash
washeluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record: ord-5020b61b6ef9458aa33103cfb2d78fbb
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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