Formaldehyde → HCID 24989849, compound

HRID 643021Notes

Reaction equation

HRID 643021 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][C:23]4=[O:28])=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.C=O.[BH3-][C:32]#N.[Na+]>C(O)(=O)C>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][N:25]([CH3:32])[CH2:24][C:23]4=[O:28])=[CH:20][CH:21]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 24989848HCID 24989848, compound

Product 1

HCID 24989849HCID 24989849, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Chloro-N-((1-(4-(2-oxopiperazin-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (24 mg, 0.06 mmol, prepared as shown in Example 60) was stirred in 2 mL acetic acid at RT. To it was added formaldehyde (37% in water, 22 μL, 0.3 mmol). The mixture was stirred for 10 min. NaBH3CN (30 mg, 0.48 mmol) was added. The reaction was allowed for 10 min, and directly subjected to reverse phase prep HPLC to isolate the title compound. MS found for C19H19ClN6O2S (M+H)+ 431.1, 433.1 (Cl pattern).

Workup

  1. waitThe reaction was allowed for 10 min

Sources & evidence

ORD record
ord-2854cf15101c41e3ab8e0e5fc8ddd51f
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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