Formaldehyde → HCID 68857498, compound

HRID 1986300Notes

Reaction equation

HRID 1986300 reaction equation
[Cl:1][C:2]1[C:3]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:29]([C:30](=[O:35])[NH:31][CH:32]4[CH2:34][CH2:33]4)[C:23]=3[CH:22]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])=[N:6][CH:7]=1.C=O.[C:38](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CO>[Cl:1][C:2]1[C:3]([C:21]2[S:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:29]([C:30](=[O:35])[NH:31][CH:32]4[CH2:34][CH2:33]4)[C:23]=3[CH:22]=2)=[N:4][C:5]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH:15]2[CH2:16][CH2:17][N:18]([CH3:38])[CH2:19][CH2:20]2)=[O:14])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86625388HCID 86625388, compound

Product 1

HCID 68857498HCID 68857498, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

A stirred suspension of piperidine-4-carboxylic acid {3-[5-chloro-4-(4-cyclopropylcarbamoylbenzo[b]thiophen-2-yl)-pyrimidin-2-ylamino]-propyl}-amide (231 mg, 0.450 mmol) in 1,2-dichloroethane (3 mL) and methanol (3 mL) is treated at room temperature with aqueous 37% formaldehyde (0.200 mL, 3.02 mmol) in the presence of sodium triacetoxyborohydride (165 mg, 0.779 mmol) for 24 hours. The mixture is then concentrated under reduced pressure, and subjected to chromatographic purification on silica gel, eluting with 2 M NH3/MeOH in dichloromethane: 8-15%, to provide the title compound (40 mg, 17% yield). ES+(m/z) 527 (35Cl) and 529 (37Cl) [M+H].

Workup

  1. concentrationThe mixture is then concentrated under reduced pressure
  2. customsubjected to chromatographic purification on silica gel
  3. washeluting with 2 M NH3/MeOH in dichloromethane

Sources & evidence

ORD record
ord-58a3c799e2054b069b9bd378b09022c8
Source dataset
uspto-grants-2009_06
Patent number
US07547691B2

Reaction notes

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