Trifluoroacetic acid → HCID 53386310, compound

HRID 1898534Notes

Reaction equation

HRID 1898534 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:26]([OH:28])=O)[CH2:22][CH:23]([CH3:25])[CH3:24])([O:15]C(C)(C)C)=O.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:45][N:46]1[CH:50]=[C:49]([C:51]2[N:56]=[C:55]3[C:57](C(O)=O)=[CH:58][N:59](COCC[Si](C)(C)C)[C:54]3=[N:53][CH:52]=2)[CH:48]=[N:47]1.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:26]([C@H:21]([NH:20][C:13]([C:57]2[C:55]3[C:54](=[N:53][CH:52]=[C:51]([C:49]4[CH:48]=[N:47][N:46]([CH3:45])[CH:50]=4)[N:56]=3)[NH:59][CH:58]=2)=[O:15])[CH2:22][CH:23]([CH3:24])[CH3:25])=[O:28])[CH2:5]1)#[N:3]

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 637604tert-Butoxycarbonyl-D-leucineHCID 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 670089372-(1-methyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Product 1

HCID 53386310HCID 53386310, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyanoazetidine hydrochloride for pyrrolidine, Boc-D-leucine 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 in place of hydrochloric acid for all N-Boc deprotection steps. MS: (M+H)+=421.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5a658f810a334b289e18da7d82e8afc4
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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