Dimethylamine → (dimethylcarbamoyl-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-methyl)-methyl-carbamic acid tert-butyl ester

HRID 886601Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH:10]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[N:27][N:26]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[C:23]3=[N:24][CH:25]=2)[CH:15]=1)[C:11](O)=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:45][NH:46][CH3:47].C(N(C(C)C)CC)(C)C>C1COCC1>[C:1]([O:5][C:6](=[O:7])[N:8]([CH:10]([C:11](=[O:12])[N:46]([CH3:47])[CH3:45])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[N:27][N:26]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:43])[CH3:44])[C:23]3=[N:24][CH:25]=2)[CH:15]=1)[CH3:9])([CH3:3])([CH3:2])[CH3:4]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (tert-butoxycarbonyl-methyl-amino)-{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-acetic acid, (100 mg, 0.16 mmol), dimethylamine (2 N in THF, 0.12 mL, 0.24 mmol), and diisopropylethylamine (31 mg, 0.24 mmol) in THF (2 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate (91 mg, 0.24 mmol.). The resulting suspension was heated to 60° C. with stirring until all was dissolved. The solvent was evaporated and the residue was used in next step without purification. MS: m/z 646 (M+H+).

Workup

dissolutionall was dissolved
customThe solvent was evaporated
customthe residue was used in next step without purification

Sources & evidence

ORD record: ord-0e4cd5bc9e6d435c9a422324d90273fe
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242280B2

Reaction notes

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