tert-Butanol → HCID 58447005, compound

HRID 1045756Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[N:16]([CH:25]=[C:26](C(O)=O)[N:27]=3)[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.C([N:50]([CH2:53]C)CC)C.[C:55]([OH:59])([CH3:58])([CH3:57])[CH3:56]>>[C:55]([O:59][C:53]([NH:50][C:26]1[N:27]=[C:15]2[C:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:9][CH2:10]3)=[N:19][CH:18]=[C:17]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[N:16]2[CH:25]=1)=[O:38])([CH3:58])([CH3:57])[CH3:56]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 58447008HCID 58447008, compound

Product 1

HCID 58447005HCID 58447005, compoundYield 45%

Conditions

Temperature: 80 °C

Procedure

A 100 mL round bottom flask was charged with 8-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-(thiophen-2-yl)imidazo[1,2-a]pyrazine-2-carboxylic acid (0.57 g, 1.3 mmol), diphenyl phosphoryl azide (0.68 g, 2.5 mmol), triethylamine (0.25 g, 2.5 mmol) and tert-butanol (20 mL). The mixture was stirred at 80° C. for 16 h. Reaction progress was monitored by LC-MS. Work-up: the solvent was evaporated. The residue was purified by flash column chromatography on silica gel with a 1:20 EtOAc/petroleum ether, to afford 0.30 g (45%) of the product. MS m/z: 501 (M+H+).

Workup

customReaction progress
customthe solvent was evaporated
customThe residue was purified by flash column chromatography on silica gel with a 1:20 EtOAc/petroleum ether

Sources & evidence

ORD record: ord-1a0a5bbb8c834fe1a36ca99291cd0c86
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569300B2

Reaction notes

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