Trifluoroacetic acid → HCID 53386369, compound

HRID 1898538Notes

Reaction equation

HRID 1898538 reaction equation
Cl.[C:2]([CH:4]1[CH2:7][NH:6][CH2:5]1)#[N:3].N1CCCC1.CC(O[C:18]([NH:20][C@@H:21]([C:28]([OH:30])=O)[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[O:19])(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:47][N:48]1[CH:52]=[C:51]([C:53]2[N:58]=[C:57]3[C:59](C(O)=O)=[CH:60][N:61](COCC[Si](C)(C)C)[C:56]3=[N:55][CH:54]=2)[CH:50]=[N:49]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:28](=[O:30])[C@H:21]([NH:20][C:18]([C:59]2[C:57]3[C:56](=[N:55][CH:54]=[C:53]([C:51]4[CH:50]=[N:49][N:48]([CH3:47])[CH:52]=4)[N:58]=3)[NH:61][CH:60]=2)=[O:19])[CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]2)[CH2:5]1)#[N:3]

Participants

8

Reactant 7

HCID 6422Trifluoroacetic acidHCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7014890(2R)-[(tert-Butoxycarbonyl)amino](cyclohexyl)acetic 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 53386369HCID 53386369, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyanoazetidine hydrochloride for pyrrolidine, Boc-D-cyclohexyl 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 in place of hydrochloric acid for all N-Boc deprotection steps. MS: (M+H)+=447.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-41a5f8ac5f4c40118b32f29556c6ff08
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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