Formaldehyde → HCID 178484825, compound

HRID 628441Notes

Reaction equation

HRID 628441 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([N:22]1[C:26]2[CH:27]=[C:28]([NH:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([NH2:42])[CH2:38][CH2:37]3)[C:29]3[N:30]([C:31]([CH3:34])=[N:32][N:33]=3)[C:25]=2[CH:24]=[C:23]1[CH3:43])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C=O>C(Cl)Cl>[CH2:15]([N:22]1[C:26]2[CH:27]=[C:28]([NH:35][C@H:36]3[CH2:41][CH2:40][C@H:39]([NH:42][CH3:1])[CH2:38][CH2:37]3)[C:29]3[N:30]([C:31]([CH3:34])=[N:32][N:33]=3)[C:25]=2[CH:24]=[C:23]1[CH3:43])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178422059HCID 178422059, compound

Product 1

HCID 178484825HCID 178484825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (11 mg, 0.053 mmol) was added to a mixture of trans-N-(6-benzyl-1,7-dimethyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridin-4-yl)cyclohexane-1,4-diamine (10. mg, 0.027 mmol, from Example 217) and formaldehyde solution (37 wt % in water, 3.2 mg, 0.040 mmol, Aldrich) in DCM (0.5 mL). After 30 minutes, both monomethylated and dimethylated products were observed by LCMS. Purification via preparative HPLC-MS (Waters XBridge C18, eluting with a gradient of MeCN/H2O containing 0.15% NH4OH) afforded monomethylated product. (Yield: 0.8 mg, 7%).

Workup

  1. customPurification via preparative HPLC-MS (Waters XBridge C18
  2. washeluting with a gradient of MeCN/H2O containing 0.15% NH4OH)
  3. customafforded monomethylated product

Sources & evidence

ORD record
ord-93a33d255eba449dbbf51b650dcfc539
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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