Dichloromethane → HCID 66824190, compound

HRID 1692899Notes

Reaction equation

[C:1]([CH2:3][C:4]1([N:15]2[CH:19]=[C:18]([C:20]3[C:21]4[CH:28]=[CH:27][N:26](COCC[Si](C)(C)C)[C:22]=4[N:23]=[CH:24][N:25]=3)[CH:17]=[N:16]2)[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)#[N:2].C(Cl)Cl.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[N:23]1[C:22]2[NH:26][CH:27]=[CH:28][C:21]=2[C:20]([C:18]2[CH:17]=[N:16][N:15]([C:4]3([CH2:3][C:1]#[N:2])[CH2:7][NH:6][CH2:5]3)[CH:19]=2)=[N:25][CH:24]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 57868843tert-Butyl 3-(cyanomethyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

Product 1

HCID 66824190HCID 66824190, compoundYield 88%

Procedure

A solution of tert-butyl 3-(cyanomethyl)-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidine-1-carboxylate, as prepared in Example 1, Step 2 (0.60 g, 1.2 mmol) in trifluoroacetic acid (10 mL) and methylene chloride (40 mL) was stirred for 5 hours. The solvents were removed in vacuo and the residue stirred in a solution of methanol (40 mL) and 14.50 M of ammonium hydroxide in water (10 mL) overnight. The solvent was evaporated, the residue reconstituted in methanol and purified by preparative-HPLC/MS (SunFire C18 column, eluting with a gradient of MeCN/H2O containing 0.1% TFA) to afford the product as the trifluoroacetic acid salt (526 mg, 88%).

Workup

customThe solvents were removed in vacuo
customThe solvent was evaporated
custompurified by preparative-HPLC/MS (SunFire C18 column
washeluting with a gradient of MeCN/H2O containing 0.1% TFA)

Sources & evidence

ORD record: ord-e5139f5992f143afbb12addf7b3ab010
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158616B2

Reaction notes

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