Trifluoroacetic acid → HCID 53386254, compound

HRID 1898524Notes

Reaction equation

HRID 1898524 reaction equation
Cl.[C:2]([CH:4]1[CH2:7][NH:6][CH2:5]1)#[N:3].N1CCCC1.[C:13]([NH:20][C@@H:21]([C:23]([OH:25])=O)[CH3:22])([O:15]C(C)(C)C)=O.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH2:42]([N:44]1[CH:48]=[C:47]([C:49]2[N:54]=[C:53]3[C:55](C(O)=O)=[CH:56][N:57](COCC[Si](C)(C)C)[C:52]3=[N:51][CH:50]=2)[CH:46]=[N:45]1)[CH3:43].C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)C(O)=O>>[C:2]([CH:4]1[CH2:7][N:6]([C:23](=[O:25])[C@H:21]([NH:20][C:13]([C:55]2[C:53]3[C:52](=[N:51][CH:50]=[C:49]([C:47]4[CH:46]=[N:45][N:44]([CH2:42][CH3:43])[CH:48]=4)[N:54]=3)[NH:57][CH:56]=2)=[O:15])[CH3:22])[CH2:5]1)#[N:3]

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 637606BOC-D-alanineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 45072465Azetidine-3-carbonitrile 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 53386254HCID 53386254, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyanoazetidine hydrochloride 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)+=393.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-075c867383404a17852c156c6fe363b1
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…