2,2,2-Trifluoroethanol → HCID 58438543, compound

HRID 1898560Notes

Reaction equation

HRID 1898560 reaction equation
Cl.[C:2]([C:4]1([CH3:8])[CH2:7][NH:6][CH2:5]1)#[N:3].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>>[C:2]([C:4]1([CH3:8])[CH2:7][N:6]([C:26](=[O:28])[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])[CH:23]2[CH2:24][CH2:25]2)[CH2:5]1)#[N:3]

Participants

8

Reactant 7

HCID 64092,2,2-TrifluoroethanolHCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 575166233-Methylazetidine-3-carbonitrile--hydrogen chloride (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 58438543HCID 58438543, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyano-3-methyl-azetidine hydrochloride 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. MS: (M+H)+=419.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5ff1e6e03cd2424c8f46b5d350ddc51d
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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