Trifluoroacetic acid → HCID 53386155, compound

HRID 1898516Notes

Reaction equation

HRID 1898516 reaction equation
Cl.[C:2]([CH:4]1[CH2:7][NH:6][CH2:5]1)#[N:3].[NH:8]1CCCC1.[CH3:13][N:14]1[CH:18]=[C:17]([C:19]2[N:24]=[C:23]3[C:25]([C:36]([OH:38])=O)=[CH:26][N:27](COCC[Si](C)(C)C)[C:22]3=[N:21][CH:20]=2)[CH:16]=[N:15]1.[CH:39]1([C:42]2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)[CH2:41][CH2:40]1.F[C:63](F)(F)[C:64]([OH:66])=O>>[C:2]([CH:4]1[CH2:7][N:6]([C:64]([C@H:63]([NH:8][C:36]([C:25]2[C:23]3[C:22](=[N:21][CH:20]=[C:19]([C:17]4[CH:16]=[N:15][N:14]([CH3:13])[CH:18]=4)[N:24]=3)[NH:27][CH:26]=2)=[O:38])[C:39]([CH3:42])([CH3:41])[CH3:40])=[O:66])[CH2:5]1)#[N:3]

Participants

6

Reactant 5

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 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 53386155HCID 53386155, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyanoazetidine hydrochloride 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)+=421.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2c532955ad6a47238f71c871ac8a1567
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…