Trifluoroacetic acid → HCID 58438540, compound

HRID 1898567Notes

Reaction equation

HRID 1898567 reaction equation
Cl.[F:2][C:3]1([F:7])[CH2:6][NH:5][CH2:4]1.N1CCCC1.CC(O[C:18]([NH:20][C@@H:21]([C:25]([OH:27])=O)[CH:22]1[CH2:24][CH2:23]1)=[O:19])(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:44][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.C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)C(O)=O>>[CH:22]1([C@@H:21]([NH:20][C:18]([C:56]2[C:54]3[C:53](=[N:52][CH:51]=[C:50]([C:48]4[CH:47]=[N:46][N:45]([CH3:44])[CH:49]=4)[N:55]=3)[NH:58][CH:57]=2)=[O:19])[C:25]([N:5]2[CH2:6][C:3]([F:7])([F:2])[CH2:4]2)=[O:27])[CH2:23][CH2:24]1

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 670089372-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Product 1

HCID 58438540HCID 58438540, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3,3-difluoroazetidine hydrochloride for pyrrolidine, Boc-D-cyclopropyl glycine for Boc-D-tert-leucine, and 2-(1-methyl-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 instead of hydrochloric acid for all N-Boc deprotection steps. MS: (M+H)+=416.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-73448b9542c1499d93ee4aec591d3a2f
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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