Trifluoroacetic acid → HCID 58438559, compound

HRID 1898570Notes

Reaction equation

HRID 1898570 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[C:8]([C:10]1([CH2:14][CH3:15])[CH2:13][NH:12][CH2:11]1)#[N:9].N1CCCC1.CC(OC([NH:28][C@@H:29]([C:33]([OH:35])=O)[CH:30]1[CH2:32][CH2:31]1)=O)(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:52][N:53]1[CH:57]=[C:56]([C:58]2[N:63]=[C:62]3C(C(O)=O)=[CH:65][N:66](COCC[Si](C)(C)C)[C:61]3=[N:60][CH:59]=2)[CH:55]=[N:54]1.C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)C(O)=O>>[C:8]([C:10]1([CH2:14][CH3:15])[CH2:13][N:12]([C:33](=[O:35])[C@H:29]([NH:28][C:3]([C:2]2[C:62]3[C:61](=[N:60][CH:59]=[C:58]([C:56]4[CH:55]=[N:54][N:53]([CH3:52])[CH:57]=4)[N:63]=3)[NH:66][CH:65]=2)=[O:5])[CH:30]2[CH2:31][CH2:32]2)[CH2:11]1)#[N:9]

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 670089372-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acidHCID 67386573HCID 67386573, compound

Product 1

HCID 58438559HCID 58438559, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyano-3-ethyl-azetidine trifluoroacetate 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)+=433.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c8006604c5b649149e7be89f9848c27a
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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