Diisopropylethylamine → HCID 117914857, compound

HRID 1772167Notes

Reaction equation

[CH2:1]1[C:9]2[CH:8]=[C:7]([C:10](Cl)=[O:11])[N:6]=[CH:5][C:4]=2[CH2:3][O:2]1.[C:13]([O:17][C:18](=[O:44])[N:19]([CH:21]([C:23](=[O:43])[NH:24][C:25]1[CH:30]=[C:29]([C:31]2[C:40]([CH3:41])=[CH:39][CH:38]=[C:37]3[C:32]=2[CH:33]=[CH:34][CH:35]=[N:36]3)[CH:28]=[C:27]([NH2:42])[N:26]=1)[CH3:22])[CH3:20])([CH3:16])([CH3:15])[CH3:14].CCN(C(C)C)C(C)C>C1COCC1>[C:13]([O:17][C:18](=[O:44])[N:19]([CH:21]([C:23](=[O:43])[NH:24][C:25]1[CH:30]=[C:29]([C:31]2[C:40]([CH3:41])=[CH:39][CH:38]=[C:37]3[C:32]=2[CH:33]=[CH:34][CH:35]=[N:36]3)[CH:28]=[C:27]([NH:42][C:10]([C:7]2[N:6]=[CH:5][C:4]3[CH2:3][O:2][CH2:1][C:9]=3[CH:8]=2)=[O:11])[N:26]=1)[CH3:22])[CH3:20])([CH3:14])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

1H,3H-furo[3,4-c]pyridine-6-carbonyl chloride M1 (33 mg, 0.2 mmol) is added to tert-butyl-N-(1-{[6-amino-4-(6-methylquinolin-5-yl)pyridin-2-yl]carbamoyl}ethyl)-N-methyl-carbamate J1 (60 mg, 0.14 mmol) and DIPEA (59 μl, 0.34 mmol) in THF (1 ml) and the mixture is stirred at 50° C. for 2 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 17 mg (21%). HPLC-MS: M+H=583; tR=1.01 min (Method—2).

Workup

concentrationThe mixture is concentrated in vacuo
customthe product purified by RP HPLC

Sources & evidence

ORD record: ord-e56d2f3d251b460780e5b88cfd7e1949
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249151B2

Reaction notes

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