Potassium Carbonate → tert-Butyl 4-(5-(8-morpholino-2-(quinoline-2-carboxamido)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

HRID 1772637Notes

Reaction equation

HRID 1772637 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([NH:11][C:12]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]=3)=[O:13])[N:10]=[C:6]2[C:5]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:38]2[CH:39]=[CH:40][C:41]([N:44]3[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]3)=[N:42][CH:43]=2)O1.C([O-])([O-])=O.[K+].[K+]>>[O:27]1[CH2:28][CH2:29][N:24]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([NH:11][C:12]([C:14]4[CH:23]=[CH:22][C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[N:15]=4)=[O:13])[N:10]=3)[C:2]([C:38]3[CH:39]=[CH:40][C:41]([N:44]4[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]4)=[N:42][CH:43]=3)=[CH:3][N:4]=2)[CH2:25][CH2:26]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 16217947Tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylateHCID 117728149N-(5-Bromo-8-morpholinoimidazo[1,2-a]pyrazin-2-yl)quinoline-2-carboxamide

Product 1

HCID 117732270tert-Butyl 4-(5-(8-morpholino-2-(quinoline-2-carboxamido)imidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Procedure

Compound 21d was prepared from compound 21c and tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate using the reaction conditions described in Example 1, Step G, and substituting K2CO3 as the base. Mass Spectrum (LCMS, ESI pos.) Calcd. For C34H37N9O4: 636.3 (M+H). Found 636.4.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-3fc93d21dfd94b279f7a33aa35d154c0
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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