Sodium cyanoborohydride → HCID 68803960, compound

HRID 1670733Notes

Reaction equation

HRID 1670733 reaction equation
BrC1C=C([Cl:27])C=C2C=1NCCC2[NH:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1[NH:22][C:21]2[CH:23]=[CH:24][S:25][C:20]=2[C:19](=[O:26])[CH:18]=1.C[O-].[Na+].BrC1C=C([Cl:43])C=C2C=1NCCC2=O.C([BH3-])#N.[Na+]>CO>[ClH:27].[ClH:43].[NH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1[NH:22][C:21]2[CH:23]=[CH:24][S:25][C:20]=2[C:19](=[O:26])[CH:18]=1

Participants

6

Reactant 4

HCID 5003444Sodium cyanoborohydride2×HCID 10942334Sodium MethoxideHCID 24803778HCID 24803778, compoundHCID 53769387HCID 53769387, compound

Product 1

HCID 68803960HCID 68803960, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A representative example of method E is as follows. Preparation of 5-[3-(8-Bromo-6-chloro-1,2,3,4-tetrahydro-quinolin-4-ylamino)-propylamino]-4H-thieno[3,2-b]pyridin-7-one: A solution of 5-(3-Amino-propylamino)-4H-thieno[3,2-b]pyridine-7-one di-hydrochloride (XVIII) in methanol (0.08M) was prepared and then treated with sodium methoxide (2 equivalents, 0.5M in methanol). 8-Bromo-6-chloro-2,3-dihydro-1H-quinolin-4-one (1 equivalent) was added as a solid. Sodium cyanoborohydride (3 equivalents) was added as a solid. The mixture was then refluxed for 20 hours, adding an additional equivalent of sodium cyanoborohydride after 16 hours. The reaction mix was poured onto a column of silica gel and the product was eluted with 10% NH3 (sat.)/MeOH and dichloromethane. Solvent was then removed in vacuo. Purification of the crude product was accomplished by flash chromatography, product eluted with a gradient of 0-12% NH3 (sat.)/MeOH and dichloromethane. The resulting solid was triturated with ether, isolated by filtration, and dried to give the title compound as a white solid (formula XIX, X═NH).

Workup

  1. temperatureThe mixture was then refluxed for 20 hours
  2. additionThe reaction mix
  3. additionwas poured onto a column of silica gel
  4. washthe product was eluted with 10% NH3 (sat.)/MeOH and dichloromethane
  5. customSolvent was then removed in vacuo
  6. customPurification of the crude product
  7. washeluted with a gradient of 0-12% NH3 (sat.)/MeOH and dichloromethane
  8. customThe resulting solid was triturated with ether
  9. customisolated by filtration
  10. customdried

Sources & evidence

ORD record
ord-ec5c2cd968414d579fe658ca1286e96d
Source dataset
uspto-grants-2011_08
Patent number
US07994192B2

Reaction notes

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