3-tert-Butyl-5-(pyrrolidin-1-ylmethyl)benzoic acid trifluoroacetate → 3-tert-Butyl-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pyrrolidin-1-ylmethyl)benzamide

HRID 1055737Notes

Reaction equation

HRID 1055737 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N:9]1[C:16]2[N:12]([N:13]=[C:14]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:15]=2)[CH:11]=[CH:10]1.FC(F)(F)C(O)=O.[C:30]([C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([CH2:43][N:44]2[CH2:48][CH2:47][CH2:46][CH2:45]2)[CH:42]=1)[C:37](O)=[O:38])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([CH2:43][N:44]2[CH2:45][CH2:46][CH2:47][CH2:48]2)[CH:42]=1)[C:37]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([N:9]2[C:16]3[N:12]([N:13]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:15]=3)[CH:11]=[CH:10]2)[CH:4]=1)=[O:38])([CH3:33])([CH3:31])[CH3:32]

Participants

3

Reactant 2

HCID 896998093-tert-Butyl-5-(pyrrolidin-1-ylmethyl)benzoic acid trifluoroacetateHCID 897000234-Methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]aniline

Product 1

HCID 896997593-tert-Butyl-N-{4-methyl-3-[6-(pyridin-3-yl)-1H-imidazo[1,2-b]pyrazol-1-yl]phenyl}-5-(pyrrolidin-1-ylmethyl)benzamide

Procedure

35 mg (0.12 mmol) of the compound of Example 6A and 47 mg (0.12 mmol) of the compound of Example 22A were reacted and worked up analogously to the procedure of Example 16. This gave 55 mg (95% pure, 81% of theory) of the title compound.

Sources & evidence

ORD record
ord-f938a31b79ff49c0b537506c507a0489
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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