Formaldehyde → HCID 59993290, compound

HRID 238230Notes

Reaction equation

HRID 238230 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][CH:19]([C:21]3[N:30]([CH3:31])[C:29](=[O:32])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH3:20])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C=O.[CH3:35]N(C=O)C.C([BH3-])#N>CC#N>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:13][CH2:14][CH:15]([N:18]([CH3:35])[CH:19]([C:21]3[N:30]([CH3:31])[C:29](=[O:32])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH3:20])[CH2:16][CH2:17]2)(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6228DimethylformamideHCID 498716Cyano-borohydrideHCID 59993356HCID 59993356, compound

Product 1

HCID 59993290HCID 59993290, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-{1-[1-(4-methoxy-benzenesulfonyl)-piperidin-4-ylamino]-ethyl}-3-methyl-3H-quinazolin-4-one (183 mg, 0.4 mmol), formaldehyde (39 μL, 0.48 mmol, 37% wt. solution in water) and DMF (1 mL) was added MP-Cyanoborohydride (300 mg, 2-3 mmol/g) and the reaction was stirred overnight at room temperature. The reaction mixture was then filtered and purified by HPLC to yield the product. HPLC ret. time 2.41 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, CDCl3) δ 8.28 (d, J=8.0 Hz, 1H), 7.93 (t, J=7.2 Hz, 1H), 7.68 (m, 4H), 7.03 (d, J=8.6 Hz, 2H), 4.93 (m, 1H), 3.98 (s, 1H), 3.89 (s, 3H), 3.69 (s, 3H), 3.10 (s, 3H), 2.58 (m, 2H), 2.21 (m, 2H), 1.78 (d, J=6.6 Hz, 3H), 1.31 (m, 4H); ESI-MS m/z 471.3 (M+1)+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. custompurified by HPLC
  3. customto yield the product

Sources & evidence

ORD record
ord-395625dd0afe4030aaa0fe575ed061f3
Source dataset
uspto-grants-2014_02
Patent number
US08642609B2

Reaction notes

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