Hydrochloric Acid → HCID 67005878, compound

HRID 564650Notes

Reaction equation

HRID 564650 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][NH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=O)[CH:19]=3)=[O:17])[CH:9]=2)=[CH:4][C:3]=1[CH2:26][N:27]1[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[C@@H:29]([CH3:40])[CH2:28]1.[NH2:41][CH2:42][C:43]1[C:48]([CH2:49][CH3:50])=[N:47][C:46]2[N:51]([CH2:54][CH3:55])[N:52]=[CH:53][C:45]=2[C:44]=1[NH:56][CH:57]1[CH2:62][CH2:61][O:60][CH2:59][CH2:58]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl.O>[CH2:54]([N:51]1[C:46]2=[N:47][C:48]([CH2:49][CH3:50])=[C:43]([CH2:42][NH:41][CH2:24][C:20]3[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=3)[C:16]([NH:15][CH2:14][C:10]3[CH:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[C:3]([CH2:26][N:27]5[CH2:32][CH2:31][NH:30][C@@H:29]([CH3:40])[CH2:28]5)[CH:4]=4)[CH:13]=[CH:12][CH:11]=3)=[O:17])[C:44]([NH:56][CH:57]3[CH2:58][CH2:59][O:60][CH2:61][CH2:62]3)=[C:45]2[CH:53]=[N:52]1)[CH3:55]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 57813546HCID 57813546, compoundHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 67005878HCID 67005878, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S)-4-{[4-fluoro-3′-({[(3-formylphenyl)-carbonyl]amino}methyl)-3-biphenylyl]methyl}-2-methyl-1-piperazinecarboxylate (195 mg, 0.36 mmol) in dichloromethane (5 mL) was added 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine, and (110 mg, 0.36 mmol) and sodium triacetoxyborohydride (115 mg. 0.54 mmol) and the resulting solution was stirred at ambient temperature for 16 h and then treated with aqueous hydrochloric acid (2M, 2 mL) and stirred for a further 2 h. The mixture was treated with water (20 mL) and extracted with dichloromethane (25 mL). The organic phase was concentrated to dryness and the residue dissolved in methanol (5 mL), treated with aqueous hydrochloric acid (2M, 2 mL) and stirred at ambient temperature for 16 h. The mixture was then concentrated to dryness and the product purified by mass-directed automated preparative HPLC. Product-containing fractions were concentrated to dryness to afford 25 mg of the title compound. LC-MS m/z 733 (M+H)+, 0.79 min (ret time).

Workup

  1. stirringstirred for a further 2 h
  2. extractionextracted with dichloromethane (25 mL)
  3. concentrationThe organic phase was concentrated to dryness
  4. dissolutionthe residue dissolved in methanol (5 mL)
  5. additiontreated with aqueous hydrochloric acid (2M, 2 mL)
  6. stirringstirred at ambient temperature for 16 h
  7. concentrationThe mixture was then concentrated to dryness
  8. customthe product purified
  9. concentrationProduct-containing fractions were concentrated to dryness

Sources & evidence

ORD record
ord-700a5e61de4a4a58a05115392de7cd24
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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