Trifluoroacetic acid → HCID 58438591, compound

HRID 1898566Notes

Reaction equation

HRID 1898566 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[CH3:8][C:9]1([OH:13])[CH2:12][NH:11][CH2:10]1.N1CCCC1.CC(OC([NH:26][C@@H:27]([C:31]([OH:33])=O)[CH:28]1[CH2:30][CH2:29]1)=O)(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH2:50]([N:52]1[CH:56]=[C:55]([C:57]2[N:62]=[C:61]3C(C(O)=O)=[CH:64][N:65](COCC[Si](C)(C)C)[C:60]3=[N:59][CH:58]=2)[CH:54]=[N:53]1)[CH3:51].C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)C(O)=O>>[CH:28]1([C@@H:27]([NH:26][C:3]([C:2]2[C:61]3[C:60](=[N:59][CH:58]=[C:57]([C:55]4[CH:54]=[N:53][N:52]([CH2:50][CH3:51])[CH:56]=4)[N:62]=3)[NH:65][CH:64]=2)=[O:5])[C:31]([N:11]2[CH2:12][C:9]([OH:13])([CH3:8])[CH2:10]2)=[O:33])[CH2:29][CH2:30]1

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 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 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidHCID 668475833-methylazetidin-3-ol: trifluoroacetic acid

Product 1

HCID 58438591HCID 58438591, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-methyl-azetidin-3-ol trifluoroacetate 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. Trifluoroacetic acid was used instead of hydrochloric acid for all N-Boc deprotection steps. MS: (M+H)+=424.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-1cf448e57df24e73a2737867b0d5d69c
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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