2,2,2-Trifluoroethanol → HCID 58438620, compound

HRID 1898561Notes

Reaction equation

HRID 1898561 reaction equation
Cl.[C:2]([C:4]1([CH3:8])[CH2:7][NH:6][CH2:5]1)#[N:3].[NH:9]1CCCC1.[CH3:14][N:15]1[CH:19]=[C:18]([C:20]2[N:25]=[C:24]3[C:26]([C:37]([OH:39])=O)=[CH:27][N:28](COCC[Si](C)(C)C)[C:23]3=[N:22][CH:21]=2)[CH:17]=[N:16]1.[CH:40]1([C:43]2N=C3C(C(O)=O)=CN(COCC[Si](C)(C)C)C3=NC=2)[CH2:42][CH2:41]1.F[C:64](F)(F)[CH2:65][OH:66]>>[C:2]([C:4]1([CH3:8])[CH2:7][N:6]([C:65]([C@H:64]([NH:9][C:37]([C:26]2[C:24]3[C:23](=[N:22][CH:21]=[C:20]([C:18]4[CH:17]=[N:16][N:15]([CH3:14])[CH:19]=4)[N:25]=3)[NH:28][CH:27]=2)=[O:39])[C:40]([CH3:43])([CH3:42])[CH3:41])=[O:66])[CH2:5]1)#[N:3]

Participants

6

Reactant 5

HCID 64092,2,2-TrifluoroethanolHCID 31268PyrrolidineHCID 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 58438620HCID 58438620, compound

Procedure

Prepared according to the procedure outlined in Example 1 substituting 3-cyano-3-methyl-azetidine hydrochloride for pyrrolidine 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)+=435.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-fea6a715699742ae990cbc125ce75e33
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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