1-Cyanocyclopropanecarboxylic acid → HCID 118253709, compound

HRID 1487336Notes

Reaction equation

HRID 1487336 reaction equation
Br[C:2]1[N:3]=[C:4]2[C:9]([NH:10][C@H:11]3[C@@H:15]([CH2:16][F:17])[CH2:14][N:13]([C:18]([O:20]C(C)(C)C)=O)[CH2:12]3)=[C:8]([C:25](=[O:27])[NH2:26])[CH:7]=[N:6][N:5]2[CH:28]=1.[CH2:29]([N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)C.[C:45]([C:47]1(C(O)=O)[CH2:49][CH2:48]1)#[N:46]>>[C:45]([C:47]1([C:18]([N:13]2[CH2:14][C@H:15]([CH2:16][F:17])[C@H:11]([NH:10][C:9]3[C:4]4[N:5]([CH:28]=[C:2]([C:34]5[CH:33]=[N:32][N:31]([CH3:29])[CH:35]=5)[N:3]=4)[N:6]=[CH:7][C:8]=3[C:25]([NH2:26])=[O:27])[CH2:12]2)=[O:20])[CH2:49][CH2:48]1)#[N:46]

Participants

4

Reactant 3

HCID 27332591-Cyanocyclopropanecarboxylic acidHCID 113790451-Ethyl-1H-pyrazole-4-boronic acid, pinacol esterHCID 89995574HCID 89995574, compound

Product 1

HCID 118253709HCID 118253709, compound

Procedure

According to the procedure described for Example 56, Example 57 was prepared from (3S,4S)-tert-butyl 3-((2-bromo-7-carbamoylimidazo[1,2-b]pyridazin-8-yl)amino)-4-(fluoromethyl)pyrrolidine-1-carboxylate (from Step 2 of Example 56) via Suzuki coupling reaction with 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole under conditions similar to Step 3 of Example 56, deprotection of N-Boc under conditions similar to Step 3 of Example 56 and amidation with 1-cyanocyclopropanecarboxylic acid under conditions similar to Step 5 of Example 56.

Sources & evidence

ORD record
ord-db6047cb55bb480f8d3c5f85e0032c9a
Source dataset
uspto-grants-2016_08
Patent number
US09428511B2

Reaction notes

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