Trifluoroacetic acid → HCID 53386207, compound

HRID 1898521Notes

Reaction equation

HRID 1898521 reaction equation
F[C:2](F)(F)[C:3]([OH:5])=O.[NH:8]1[CH2:12][CH2:11][C@H:10]([C:13]#[N:14])[CH2:9]1.[NH:15]1CCCC1.[CH3:20][N:21]1[CH:25]=[C:24]([C:26]2[N:31]=[C:30]3[C:32]([C:43]([OH:45])=O)=[CH:33][N:34](COCC[Si](C)(C)C)[C:29]3=[N:28][CH:27]=2)[CH:23]=[N:22]1.[CH:46]1([C:49]2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)[CH2:48][CH2:47]1.FC(F)(F)C(O)=O>>[C:13]([C@H:10]1[CH2:11][CH2:12][N:8]([C:3]([C@H:2]([NH:15][C:43]([C:32]2[C:30]3[C:29](=[N:28][CH:27]=[C:26]([C:24]4[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=4)[N:31]=3)[NH:34][CH:33]=2)=[O:45])[C:46]([CH3:49])([CH3:48])[CH3:47])=[O:5])[CH2:9]1)#[N:14]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 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 67386474HCID 67386474, compound

Product 1

HCID 53386207HCID 53386207, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting (S)-pyrrolidine-3-carbonitrile trifluoroacetate for pyrrolidine 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)+=435.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-005ce23ca37347d1b453e9bdb2720721
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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