Formaldehyde → HCID 24887974, compound

HRID 1350490Notes

Reaction equation

HRID 1350490 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:16]3)[C:12]3[C:11]4[CH:30]=[CH:31][CH:32]=[CH:33][C:10]=4[S:9][C:8]=3[NH:7][C:6]=2[CH:34]=1.[C:35](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O>ClC(Cl)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:35])[C@@H:17]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)[CH2:16]3)[C:12]3[C:11]4[CH:30]=[CH:31][CH:32]=[CH:33][C:10]=4[S:9][C:8]=3[NH:7][C:6]=2[CH:34]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58860662HCID 58860662, compound

Product 1

HCID 24887974HCID 24887974, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Using a method similar to the method of Example 543, using (S)-9-fluoro-5-{3-[2-(4-fluoro-phenyl)-ethyl]-piperazin-1-yl}-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene (0.339 g, 0.714 mmol), sodium triacetoxyborohydride (0.227 g, 1.07 mmol), and aqueous formaldehyde (0.080 mL, 1.1 mmol) in dichloroethane, and employing a second chromatographic purification, eluting with a gradient of a solution of ethyl acetate: hexane (1:1) with 2% 2M ammonia in methanol (in hexane) added, gives the title compound (0.238 g). Mass spectrum (APCI+, m/e): 489 (M+1).

Workup

  1. customa second chromatographic purification
  2. washeluting with a gradient of a solution of ethyl acetate: hexane (1:1) with 2% 2M ammonia in methanol (in hexane)
  3. additionadded

Sources & evidence

ORD record
ord-33edf41420ff478d85a7c2028b49da23
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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