Dimethylformamide → HCID 86685306, compound

HRID 1852980Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.CN(C=O)C.[C:26]([CH:28]=[CH:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)#[N:27].C1CCN2C(=NCCC2)CC1>CCOC(C)=O>[C:26]([CH2:28][CH:29]([CH:30]1[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]1)[N:15]1[CH:14]=[C:13]([C:11]2[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[N:12]=2)[CH:17]=[N:16]1)#[N:27]

Participants

Conditions

Temperature: 45 °C

Procedure

To 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation K; 50 mg, 0.19 mmol) was added DMF (950 μL, 0.19 mmol), tert-butyl 4-(2-cyanovinyl)piperidine-1-carboxylate (Table 1, compound 1; 67 mg, 0.28 mmol) and DBU (185 μL, 1.3 mmol). The reaction mixture was heated to 45° C. for 8 hours, then diluted in EtOAc and washed with water and brine. The organic layer was dried with MgSO4, filtered and concentrated down to a yellow oil. Purification of the resulting crude material by reverse phase HPLC using a 0-100% acetonitrile/water gradient afforded tert-butyl 4-(2-cyano-1-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)ethyl)piperidine-1-carboxylate (59 mg, 62% yield). MS (apci) m/z=502.2 (M+H).

Workup

washwashed with water and brine
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
concentrationconcentrated down to a yellow oil
customPurification of the resulting crude material by reverse phase HPLC

Sources & evidence

ORD record: ord-37f8268a38d04b2ab947632a1dfc6a34
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962596B2

Reaction notes

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