Trifluoroacetic acid → 2-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

HRID 1898525Notes

Reaction equation

HRID 1898525 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]#[N:8])[CH2:3][CH2:2]1.N1CCCC1.[C:14]([NH:21][C@@H:22]([C:24]([OH:26])=O)[CH3:23])([O:16]C(C)(C)C)=O.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH2:43]([N:45]1[CH:49]=[C:48]([C:50]2[N:55]=[C:54]3[C:56](C(O)=O)=[CH:57][N:58](COCC[Si](C)(C)C)[C:53]3=[N:52][CH:51]=2)[CH:47]=[N:46]1)[CH3:44].C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)C(O)=O>>[C:7]([CH:4]1[CH2:5][CH2:6][N:1]([C:24](=[O:26])[C@H:22]([NH:21][C:14]([C:56]2[C:54]3[C:53](=[N:52][CH:51]=[C:50]([C:48]4[CH:47]=[N:46][N:45]([CH2:43][CH3:44])[CH:49]=4)[N:55]=3)[NH:58][CH:57]=2)=[O:16])[CH3:23])[CH2:2][CH2:3]1)#[N:8]

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 1382234-CyanopiperidineHCID 637606BOC-D-alanineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Product 1

HCID 533863082-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(4-cyano-piperidin-1-yl)-1-methyl-2-oxo-ethyl]-amide

Procedure

Prepared according to the procedure outlined in Example 1 substituting piperidine-4-carbonitrile for pyrrolidine, Boc-D-alanine for Boc-D-tert-leucine, 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-b]pyrazine-7-carboxylic acid. Trifluoroacetic acid was used in place of hydrochloric acid for all N-Boc deprotection steps. MS: (M+H)+=421.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-3923e3c9af9f472797bae7c6a6068c59
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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