2-Methoxy-N-2-pyridinyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → HCID 71226538, compound

HRID 928322Notes

Reaction equation

HRID 928322 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3C(OCC3C=CC=CC=3)=O)=[N:9][C:10]=2Br)[CH:5]=[CH:6][N:7]=1.[CH3:27][O:28][C:29]1[CH:43]=[C:42](B2OC(C)(C)C(C)(C)O2)[CH:41]=[CH:40][C:30]=1[C:31]([NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)=[O:32]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:12]3[CH2:16][CH2:15][CH2:14][NH:13]3)=[N:9][C:10]=2[C:42]2[CH:41]=[CH:40][C:30]([C:31]([NH:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[O:32])=[C:29]([O:28][CH3:27])[CH:43]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 712230672-Methoxy-N-2-pyridinyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×HCID 71233875(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate2×

Product 1

HCID 71226538HCID 71226538, compoundYield 56.6%

Procedure

This intermediate was prepared, in an analogous manner as described for intermediate 2, from (S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (Intermediate 1e) and 2-methoxy-N-(pyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (intermediate 18) to afford the title compound (175 mg, 56.6%).

Workup

  1. customThis intermediate was prepared, in an analogous manner

Sources & evidence

ORD record
ord-ccb4a4199e5b4226a0b7b7b88b0b4291
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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