Pyrrolidine → 2-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-cyclopropyl-2-(3,3-difluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-amide

HRID 1898550Notes

Reaction equation

HRID 1898550 reaction equation
Cl.[F:2][C:3]1([F:8])[CH2:7][CH2:6][NH:5][CH2:4]1.N1CCCC1.CC(O[C:19]([NH:21][C@@H:22]([C:26]([OH:28])=O)[CH:23]1[CH2:25][CH2:24]1)=[O:20])(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH2:45]([N:47]1[CH:51]=[C:50]([C:52]2[N:57]=[C:56]3[C:58](C(O)=O)=[CH:59][N:60](COCC[Si](C)(C)C)[C:55]3=[N:54][CH:53]=2)[CH:49]=[N:48]1)[CH3:46].C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1>>[CH:23]1([C@@H:22]([NH:21][C:19]([C:58]2[C:56]3[C:55](=[N:54][CH:53]=[C:52]([C:50]4[CH:49]=[N:48][N:47]([CH2:45][CH3:46])[CH:51]=4)[N:57]=3)[NH:60][CH:59]=2)=[O:20])[C:26]([N:5]2[CH2:6][CH2:7][C:3]([F:8])([F:2])[CH2:4]2)=[O:28])[CH2:24][CH2:25]1

Participants

7

Reactant 6

HCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 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 584385262-(1-Ethyl-1H-pyrazol-4-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-cyclopropyl-2-(3,3-difluoro-pyrrolidin-1-yl)-2-oxo-ethyl]-amide

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3,3-difluoropyrrolidine hydrochloride for pyrrolidine, Boc-D-cyclopropyl glycine 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. MS: (M+H)+=444.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a107f72871544aaa9e61d6a59ca6b883
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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