Sodium cyanoborohydride → HCID 86697545, compound

HRID 626853Notes

Reaction equation

HRID 626853 reaction equation
Cl.Cl.[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[CH:17]=[C:18]([Cl:30])[C:19]([C:28]#[N:29])=[C:20]4[C:26]=3[O:25][CH:24]([CH3:27])[CH2:23][NH:22][CH2:21]4)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12.O=[C:32]1[CH2:35][CH:34]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:33]1.C([BH3-])#N.[Na+]>CO.O>[NH2:3][C:4]1[N:9]=[CH:8][N:7]=[C:6]2[N:10]([CH:14]([C:16]3[C:26]4[O:25][CH:24]([CH3:27])[CH2:23][N:22]([CH:32]5[CH2:35][CH:34]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:41])([CH3:40])[CH3:42])[CH2:33]5)[CH2:21][C:20]=4[C:19]([C:28]#[N:29])=[C:18]([Cl:30])[CH:17]=3)[CH3:15])[N:11]=[C:12]([CH3:13])[C:5]=12

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 23374584tert-Butyl 3-oxocyclobutylcarbamateHCID 86697543HCID 86697543, compound

Product 1

HCID 86697545HCID 86697545, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

9-[1-(4-Amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-2-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-6-carbonitrile bishydrochloride (20 mg, 0.05 mmol) from Example 59, step 1, was dissolved in methanol (1.1 mL), and the tert-butyl (3-oxocyclobutyl)carbamate (0.019 g, 0.10 mmol) was added, followed by the sodium cyanoborohydride (0.0063 g, 0.10 mmol). The reaction was heated to 60° C. for 2 h, allowed to cool, diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated to give tert-butyl {3-[9-[1-(4-amino-3-methyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl]-7-chloro-6-cyano-2-methyl-2,3-dihydro-1,4-benzoxazepin-4(5H)-yl]cyclobutyl}carbamate. LCMS calculated for C28H36ClN8O3 (M+H)+: m/z=567.2; found: 567.3.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41e32d45ff7147be8ca91bdf5d5ca9a4
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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