(R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochloride → 2-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(3-cyano-3-fluoro-pyrrolidine-1-carbonyl)-2,2-dimethyl-propyl]-amide

HRID 1898511Notes

Reaction equation

HRID 1898511 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@H:9]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]([N:12]1[CH2:16][CH2:15][C:14]([F:19])([C:17]#[N:18])[CH2:13]1)=[O:11].Cl.N[C@H](C(C)(C)C)C(N1CCCC1)=O.[CH2:38]([N:40]1[CH:44]=[C:43]([C:45]2[N:50]=[C:49]3[C:51]([C:62](O)=[O:63])=[CH:52][N:53](COCC[Si](C)(C)C)[C:48]3=[N:47][CH:46]=2)[CH:42]=[N:41]1)[CH3:39]>>[C:17]([C:14]1([F:19])[CH2:15][CH2:16][N:12]([C:10]([C@H:9]([NH:8][C:62]([C:51]2[C:49]3[C:48](=[N:47][CH:46]=[C:45]([C:43]4[CH:42]=[N:41][N:40]([CH2:38][CH3:39])[CH:44]=4)[N:50]=3)[NH:53][CH:52]=2)=[O:63])[C:20]([CH3:23])([CH3:22])[CH3:21])=[O:11])[CH2:13]1)#[N:18]

Participants

4

Reactant 3

HCID 57516598(R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochlorideHCID 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidHCID 67386183HCID 67386183, compound

Product 1

HCID 584385882-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(3-cyano-3-fluoro-pyrrolidine-1-carbonyl)-2,2-dimethyl-propyl]-amide

Procedure

Prepared according to the procedure outlined in Example 1, steps 3-4 substituting 1-((R)-2-amino-3,3-dimethylbutanoyl)-3-fluoropyrrolidine-3-carbonitrile trifluoroacetate for (R)-2-amino-3,3-dimethyl-1-(pyrrolidin-1-yl)butan-1-one hydrochloride and 2-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid for 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2, 3-1)]pyrazine-7-carboxylic acid. MS: (M+H)+=467.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-34de4c50bab245bab41d2975e0bc6041
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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