Acetic Acid → HCID 22390530, compound

HRID 1072086Notes

Reaction equation

HRID 1072086 reaction equation
[C:1]([BH3-])#[N:2].[Na+].N[CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][N:16]3[C:21]=2[C:20]([NH:22][C:23]2[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[N:27]=[CH:26]4)=[N:19][CH:18]=[N:17]3)[CH2:8][CH2:7]1.[C:40](O)(=O)C.C=O>C(Cl)Cl>[CH3:40][N:2]([CH3:1])[CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[CH:14]=[CH:15][N:16]3[C:21]=2[C:20]([NH:22][C:23]2[CH:24]=[C:25]4[C:29](=[CH:30][CH:31]=2)[N:28]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=2)[N:27]=[CH:26]4)=[N:19][CH:18]=[N:17]3)[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10151881HCID 10151881, compound

Product 1

HCID 22390530HCID 22390530, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium cyanoborohydride (5 mg, 2 equiv.) was added to a solution of [5-(4-amino-piperidin-1-ylmethyl)-pyrrolo[2,1-f][1,2,4]triazin-4-yl]-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (20 mg, 0.042 mmole), acetic acid (3 uL), and 37% formaldehyde (7 uL, 2 equiv.) in DCM (0.3 ml) at 0° C. After 0.5 h, the reaction was removed from the ice-bath and, after an additional 4 h, was diluted with DCM and made alkaline with saturated NaCO3 solution. The organic layer was dried (Na2SO4) and the solvent was removed. The title compound (4 mg, 8%) was isolated by preparative HPLC. MS: 499 (M+H)+; HPLC Ret Time: 1.04 min (YMC ODS-A C18 S7 3.0×50 mm column, 2 min gradient, 5 ml/min).

Workup

  1. customthe reaction was removed from the ice-bath and, after an additional 4 h
  2. additionwas diluted with DCM
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-1043e217155c4593a3197fb83d885331
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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