Formaldehyde → HCID 135453333, compound

HRID 1611161Notes

Reaction equation

HRID 1611161 reaction equation
Cl.[NH2:2][C:3]1[N:10]=[C:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH2:19][CH:20]2[CH2:22][CH2:21]2)[CH:8]=[C:7]([CH:23]2[CH2:28][CH2:27][CH2:26][NH:25][CH2:24]2)[C:4]=1[C:5]#[N:6].C=O.[C:31]([BH3-])#N.[Na+]>CO>[NH2:2][C:3]1[N:10]=[C:9]([C:11]2[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][C:12]=2[O:18][CH2:19][CH:20]2[CH2:21][CH2:22]2)[CH:8]=[C:7]([CH:23]2[CH2:28][CH2:27][CH2:26][N:25]([CH3:31])[CH2:24]2)[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 136342476HCID 136342476, compound

Product 1

HCID 135453333HCID 135453333, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-(3-piperidinyl)nicotinonitrile hydrochloride (200.0 mg, 0.50 mmol) in MeOH were added formaldehyde (0.5 mL) and sodium cyanoborohydride (40.8 mg, 0.65 mmol) and stirred for 2 hrs at room temperature. The reaction was quenched by an addition of water, extracted with ethyl acetate, dried over MgSO4, filtered and evaporated. The residue was triturated with hexane and dried. The crude product was purified by preparative silica gel TLC (5% MeOH in dichloromethane) to give 2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-4-(1-methyl-3-piperidinyl)nicotinonitrile as a yellow solid. (28.5 mg, yield 15%)

Workup

  1. customThe reaction was quenched by an addition of water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was triturated with hexane
  7. customdried
  8. customThe crude product was purified by preparative silica gel TLC (5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-59ba7c6ceea449938a4fd1d54ef55d46
Source dataset
uspto-grants-2006_01
Patent number
US06984649B1

Reaction notes

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