2,2,2-Trifluoroethanol → HCID 58438631, compound

HRID 1898556Notes

Reaction equation

HRID 1898556 reaction equation
[C:1]([OH:6])(=O)[C:2](O)=O.[CH2:7]1[C:10]2([CH2:13][NH:12][CH2:11]2)[CH2:9][O:8]1.N1CCCC1.CC(OC([NH:26][C@@H:27]([C:31]([OH:33])=O)[CH:28]1[CH2:30][CH2:29]1)=O)(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:50][N:51]1[CH:55]=[C:54]([C:56]2[N:61]=[C:60]3C(C(O)=O)=[CH:63][N:64](COCC[Si](C)(C)C)[C:59]3=[N:58][CH:57]=2)[CH:53]=[N:52]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>[CH:28]1([C@@H:27]([NH:26][C:1]([C:2]2[C:60]3[C:59](=[N:58][CH:57]=[C:56]([C:54]4[CH:53]=[N:52][N:51]([CH3:50])[CH:55]=4)[N:61]=3)[NH:64][CH:63]=2)=[O:6])[C:31]([N:12]2[CH2:13][C:10]3([CH2:9][O:8][CH2:7]3)[CH2:11]2)=[O:33])[CH2:29][CH2:30]1

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 53308464Oxalic acid--2-oxa-6-azaspiro(3.3)heptane (1/1)HCID 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 58438631HCID 58438631, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the procedure outlined in Example 1 substituting 2-oxa-6-aza-spiro[3.3]heptane oxalate 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)+=422.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-af6e846db40b4ec2b4e13dea8d1d6841
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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