Formaldehyde → HCID 10207696, compound

HRID 2109616Notes

Reaction equation

HRID 2109616 reaction equation
[CH3:1][C:2]1([CH3:37])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12]([C:14]3[C:15]([NH:20][C:21]4[CH:29]=[C:28]5[C:24]([CH:25]=[N:26][NH:27]5)=[CH:23][CH:22]=4)=[N:16][CH:17]=[CH:18][CH:19]=3)=[O:13])=[CH:8][CH:9]=2)[N:4]([CH2:30][CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH2:3]1.C=O.[BH3-][C:41]#N.[Na+]>CCO>[CH3:1][C:2]1([CH3:37])[C:10]2[C:5](=[CH:6][C:7]([NH:11][C:12](=[O:13])[C:14]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]=3[NH:20][C:21]3[CH:29]=[C:28]4[C:24]([CH:25]=[N:26][NH:27]4)=[CH:23][CH:22]=3)=[CH:8][CH:9]=2)[N:4]([CH2:30][CH:31]2[CH2:36][CH2:35][N:34]([CH3:41])[CH2:33][CH2:32]2)[CH2:3]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10300352HCID 10300352, compound

Product 1

HCID 10207696HCID 10207696, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-[3,3-Dimethyl-1-(4-piperidylmethyl)indolin-6-yl][2-(1H-indazol-6-ylamino)(3-pyridyl)]carboxamide (140 mg, Example 41) was dissolved in 10 mL EtOH. Formaldehyde (10 mL, 37%) was added, followed by 100 mg of NaCNBH3. The mixture was stirred at RT overnight, and concentrated in vacuo. The crude was extracted between saturated NaHCO3 solution and EtOAc, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo to afford a yellow solid. This material was further purified by preparative HPLC to yield a white solid. MS: 510 (M+1). Calc'd. for C30H35N7O−509.6.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe crude was extracted between saturated NaHCO3 solution and EtOAc
  3. dry with materialthe resulting organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow solid
  7. customThis material was further purified by preparative HPLC
  8. customto yield a white solid

Sources & evidence

ORD record
ord-d1fec9b9cb744f1a81cfaabc90f0a1a4
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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