Dimethylformamide dimethyl acetal → HCID 59835832, compound

HRID 271738Notes

Reaction equation

[CH3:1]OC(OC)N(C)C.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:24]3[CH:25]=[CH:26][C:27]([O:31][CH2:32][CH2:33][N:34]4[CH2:38][CH2:37][CH2:36][CH2:35]4)=[C:28]([NH2:30])[CH:29]=3)=[N:20][CH:21]=2)=[CH:12][CH:11]=1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[CH:18][C:19]([C:22]#[C:23][C:24]3[CH:25]=[CH:26][C:27]([O:31][CH2:32][CH2:33][N:34]4[CH2:35][CH2:36][CH2:37][CH2:38]4)=[C:28]([NH:30][CH3:1])[CH:29]=3)=[N:20][CH:21]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under a nitrogen atmosphere 178 μL (1.35 mmol) N,N-dimethylformamide dimethylacetal are added to a solution of 100 mg (0.24 mmol) 5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-(2-pyrrolidin-1-yl-ethoxy)-phenylamine in 2 mL DMF, the reaction mixture is stirred for 5 h at 60° C. and cooled to RT overnight. Then 32 mg (0.85 mmol) NaBH4 are added and the mixture is again heated to 60° C. for 1 h. To complete the reaction a further 32 mg NaBH4 are added and the mixture is heated to 60° C. for a further 4 h. After cooling it is combined with saturated NaHCO3 solution, exhaustively extracted with EtOAc and the organic phase is dried over MgSO4. After the desiccant and solvent have been eliminated the residue is purified by HPLC.

Workup

temperaturecooled to RT overnight
temperaturethe mixture is again heated to 60° C. for 1 h
additionare added
temperaturethe mixture is heated to 60° C. for a further 4 h
temperatureAfter cooling it
extractionexhaustively extracted with EtOAc
dry with materialthe organic phase is dried over MgSO4
customis purified by HPLC

Sources & evidence

ORD record: ord-760c39226b1c4fcba0565912efcdeff1
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452911B2

Reaction notes

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