2,2,2-Trifluoroethanol → HCID 53386420, compound

HRID 1898554Notes

Reaction equation

HRID 1898554 reaction equation
[NH:1]1[CH2:5][CH2:4][C@@H:3]([C:6]#[N:7])[CH2:2]1.N1CCCC1.CC(O[C:18]([NH:20][C@@H:21]([C:25]([OH:27])=O)[CH:22]1[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.[CH3:44][N:45]1[CH:49]=[C:48]([C:50]2[N:55]=[C:54]3[C:56](C(O)=O)=[CH:57][N:58](COCC[Si](C)(C)C)[C:53]3=[N:52][CH:51]=2)[CH:47]=[N:46]1.C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1.FC(F)(F)CO.[F-].[Cs+]>C(#N)C>[C:6]([C@@H:3]1[CH2:4][CH2:5][N:1]([C:25](=[O:27])[C@H:21]([NH:20][C:18]([C:56]2[C:54]3[C:53](=[N:52][CH:51]=[C:50]([C:48]4[CH:47]=[N:46][N:45]([CH3:44])[CH:49]=4)[N:55]=3)[NH:58][CH:57]=2)=[O:19])[CH:22]2[CH2:23][CH2:24]2)[CH2:2]1)#[N:7]

Participants

10

Reactant 8

HCID 64092,2,2-TrifluoroethanolHCID 25953Cesium fluorideHCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 34180556HCID 34180556, compoundHCID 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 53386420HCID 53386420, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the procedure outlined in Example 1 substituting (R)-pyrrolidine-3-carbonitrile for pyrrolidine, Boc-D-cyclopropyl 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. N-Boc deprotection in step 2 was achieved using 2,2,2-trifluoroethanol in a microwave reactor. SEM deprotection in step 4 was achieved using CsF in refluxing acetonitrile. MS: (M+H)+=419.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-84b1c1e7cbf8469dacc2e9094de5996b
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…