4-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholine → (S)-tert-Butyl 1-(4-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)benzoyl)pyrrolidine-2-carboxylate

HRID 1772624Notes

Reaction equation

HRID 1772624 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][CH2:12][C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]=3)[N:10]=[C:6]2[C:5]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)CB([C:37]2[CH:56]=[CH:55][C:40]([C:41]([N:43]3[CH2:47][CH2:46][CH2:45][C@H:44]3[C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])=[O:42])=[CH:39][CH:38]=2)C1>>[O:26]1[CH2:27][CH2:28][N:23]([C:5]2[C:6]3[N:7]([CH:8]=[C:9]([CH2:11][CH2:12][C:13]4[CH:22]=[CH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[N:14]=4)[N:10]=3)[C:2]([C:37]3[CH:56]=[CH:55][C:40]([C:41]([N:43]4[CH2:47][CH2:46][CH2:45][C@H:44]4[C:48]([O:50][C:51]([CH3:52])([CH3:54])[CH3:53])=[O:49])=[O:42])=[CH:39][CH:38]=3)=[CH:3][N:4]=2)[CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 1177278954-(5-Bromo-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-8-yl)morpholineHCID 131734672(S)-tert-butyl 1-(4-(3,3,4,4-tetramethylborolan-1-yl)benzoyl)pyrrolidine-2-carboxylate

Product 1

HCID 86345488(S)-tert-Butyl 1-(4-(8-morpholino-2-(2-(quinolin-2-yl)ethyl)imidazo[1,2-a]pyrazin-5-yl)benzoyl)pyrrolidine-2-carboxylateYield 88.7%

Procedure

Compound 3a (250 mg, 0.570 mmol) was subjected to Suzuki coupling conditions with (S)-tert-butyl 1-(4-(3,3,4,4-tetramethylborolan-1-yl)benzoyl)pyrrolidine-2-carboxylate (686 mg, 1.71 mmol) using the reaction conditions described in Example 1, Step G to obtain compound 17b as a brown solid (320 mg, 81% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C37H40N6O4: 633.3 (M+H). Found 633.2.

Workup

  1. customthe reaction conditions

Sources & evidence

ORD record
ord-b94aae74b6744227b7db088defbefded
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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