Formaldehyde → HCID 135517319, compound

HRID 131460Notes

Reaction equation

HRID 131460 reaction equation
C=O.[CH3:3][C:4]1[S:13][C:12]2[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]=[C:7]([N:18]3[CH2:23][CH2:22][NH:21][C@@H:20]([CH2:24][OH:25])[CH2:19]3)[C:6]=2[CH:5]=1.Cl[CH:27](Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:27][N:21]1[CH2:22][CH2:23][N:18]([C:7]2[C:6]3[CH:5]=[C:4]([CH3:3])[S:13][C:12]=3[NH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[N:8]=2)[CH2:19][C@@H:20]1[CH2:24][OH:25]

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 135524559[(R)-4-(2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-yl)-piperazin-2-yl]-methanol

Product 1

HCID 135517319HCID 135517319, compound

Procedure

Add aqueous 37% formaldehyde (1.1 eqiv) to a solution of [(R)-4-(2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-yl)-piperazin-2-yl]-methanol (1 mmol) in dichloroethane (60 mL per 1 mmol non-alkylated starting material). Stir the mixture 2 minutes and add sodium triacetoxyborohydride (1.5 mmol per 1 mmol non-alkylated starting material). Stir the suspension for 30 minutes and quench with a saturated aqueous solution of sodium bicarbonate. Extract the aqueous phase 3 times with dichloromethane and combine the organic phases, dry over magnesium sulfate, filter and concentrate. Purify the residue via chromatography on silica gel (methylene chloride/methanol (90:10) affords the title compound as a yellow powder: mp 118-124° C.; 1H NMR (CDCl3) δ 2.31 (s, 3H), 2.43 (s, 3H), 2.45 (m, 1H), 2.59 (m, 1H), 2.82 (m, 1H), 3.31 (m, 1H), 3.58 (dd, 1H) 3.67-3.79 (m, 3H), 3.86 (dd, 1H), 4.96 (s, 1H), 6.30 (s, 1H), 6.60 (d, 1H), 6.87 (t, 1H), 6.96 (t, 1H), 7.01 (d, 1H); MS (APCI) m/z (rel intensity) 343 (100).

Workup

  1. stirringStir the suspension for 30 minutes
  2. customquench with a saturated aqueous solution of sodium bicarbonate
  3. extractionExtract the aqueous phase 3 times with dichloromethane
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the residue via chromatography on silica gel (methylene chloride/methanol (90:10)

Sources & evidence

ORD record
ord-05ce231a2903405d83fa39ca17cbf662
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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