Acetonitrile → tert-butyl 4-(4-(3-(tert-butoxycarbonylamino)-5-cyano-6-(2-fluoro-4-methoxyphenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate

HRID 336842Notes

Reaction equation

HRID 336842 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=O.[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=O.[NH2:35][C:36]1[NH:40][N:39]=[C:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH:37]=1.[C:49](#[N:51])[CH3:50]>>[C:44]([O:43][C:42]([NH:41][C:38]1[C:37]2[CH:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]4)=[CH:18][CH:17]=3)[C:50]([C:49]#[N:51])=[C:4]([C:3]3[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:2]=3[F:1])[NH:35][C:36]=2[NH:40][N:39]=1)=[O:48])([CH3:45])([CH3:47])[CH3:46]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 2795509Tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylateHCID 21255685Methyl 2-fluoro-4-methoxybenzoateHCID 45091900tert-butyl N-(5-amino-1H-pyrazol-3-yl)carbamate

Product 1

HCID 136352994tert-butyl 4-(4-(3-(tert-butoxycarbonylamino)-5-cyano-6-(2-fluoro-4-methoxyphenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylateYield 66%

Procedure

To a solution of 1 g (5.18 mmol) of methyl 2-fluoro-4-methoxybenzoate in 20 ml of acetonitrile are respectively added 1.62 g (5.18 mmol) of tert-butyl 4-(4-formylphenyl)piperazine-1-carboxylate and 1.11 g (5.18 mmol) of tert-butyl 5-amino-1H-pyrazol-3-ylcarbamate. The reaction mixture is refluxed for 8 h. The solution is brought to room temperature, then the solid is filtered and rinsed several times with acetonitrile to yield 2.22 g (66%) of tert-butyl 4-(4-(3-(tert-butoxycarbonylamino)-5-cyano-6-(2-fluoro-4-methoxyphenyl)-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-4-yl)phenyl)piperazine-1-carboxylate in the form of a yellow solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 8 h
  2. customis brought to room temperature
  3. filtrationthe solid is filtered
  4. washrinsed several times with acetonitrile

Sources & evidence

ORD record
ord-8af5f5d7677543ec98efe2308217ba68
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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