2,2,2-Trifluoroethanol → HCID 58438555, compound

HRID 1898558Notes

Reaction equation

HRID 1898558 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]1.N1CCCC1.CC(O[C:19]([NH:21][C@@H:22]([C:26]([OH:28])=O)[CH:23]1[CH2:25][CH2:24]1)=[O:20])(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH3:45][N:46]1[CH:50]=[C:49]([C:51]2[N:56]=[C:55]3[C:57](C(O)=O)=[CH:58][N:59](COCC[Si](C)(C)C)[C:54]3=[N:53][CH:52]=2)[CH:48]=[N:47]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:23]1([C@@H:22]([NH:21][C:19]([C:57]2[C:55]3[C:54](=[N:53][CH:52]=[C:51]([C:49]4[CH:48]=[N:47][N:46]([CH3:45])[CH:50]=4)[N:56]=3)[NH:59][CH:58]=2)=[O:20])[C:26]([N:1]2[CH2:6][CH2:5][S:4](=[O:8])(=[O:7])[CH2:3][CH2:2]2)=[O:28])[CH2:24][CH2:25]1

Participants

10

Reactant 8

HCID 64092,2,2-TrifluoroethanolHCID 25953Cesium fluorideHCID 31268PyrrolidineHCID 6484228Thiomorpholine 1,1-dioxideHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 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 58438555HCID 58438555, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Prepared according to the procedure outlined in Example 1 substituting thiomorpholine-1,1-dioxide 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)+=458.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-adca67e1aee5467bb11c377cd569b15b
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…