Pyrrolidine → HCID 58438592, compound

HRID 1898563Notes

Reaction equation

HRID 1898563 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1([OH:9])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.N1CCCC1.CC(O[C:22]([NH:24][C@@H:25]([C:29]([OH:31])=O)[CH:26]1[CH2:28][CH2:27]1)=[O:23])(C)C.C(N[C@@H](C(O)=O)C(C)(C)C)(OC(C)(C)C)=O.[CH2:48]([N:50]1[CH:54]=[C:53]([C:55]2[N:60]=[C:59]3[C:61](C(O)=O)=[CH:62][N:63](COCC[Si](C)(C)C)[C:58]3=[N:57][CH:56]=2)[CH:52]=[N:51]1)[CH3:49].C1(C2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)CC1>>[CH:26]1([C@@H:25]([NH:24][C:22]([C:61]2[C:59]3[C:58](=[N:57][CH:56]=[C:55]([C:53]4[CH:52]=[N:51][N:50]([CH2:48][CH3:49])[CH:54]=4)[N:60]=3)[NH:63][CH:62]=2)=[O:23])[C:29]([N:6]2[CH2:5][CH2:4][C:3]([OH:9])([C:2]([F:1])([F:10])[F:11])[CH2:8][CH2:7]2)=[O:31])[CH2:27][CH2:28]1

Participants

7

Reactant 6

HCID 31268PyrrolidineHCID 7005057(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acidHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acidHCID 179513214-(Trifluoromethyl)-4-piperidinolHCID 578296532-cyclopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 584385442-(1-ethyl-1H-pyrazol-4-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid

Product 1

HCID 58438592HCID 58438592, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 4-trifluoromethyl-piperidin-4-ol (Example 74, step 2) for pyrrolidine, Boc-D-cyclopropyl glycine for Boc-D-tert-leucine, and 2-(1-ethyl-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. MS: (M+H)+=506.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-5c958fbf81774b98b9280c71fae8e98d
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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