Sodium triacetoxyborohydride → 2-(5-{[Bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667797Notes

Reaction equation

HRID 1667797 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:16][C:17]3[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:18]=3[N+:25]([O-:27])=[O:26])[S:11][C:12]=2[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][CH:7]=1.Cl.Cl.Cl.[N:31]1([CH2:37][CH2:38][CH2:39][NH:40][CH2:41][CH2:42][CH2:43][N:44]2[CH2:49][CH2:48][O:47][CH2:46][CH2:45]2)[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[N:31]1([CH2:37][CH2:38][CH2:39][N:40]([CH2:23][C:21]2[CH:20]=[CH:19][C:18]([N+:25]([O-:27])=[O:26])=[C:17]([NH:16][C:10]3[S:11][C:12]([C:13]([NH2:15])=[O:14])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[N:9]=3)[CH:22]=2)[CH2:41][CH2:42][CH2:43][N:44]2[CH2:45][CH2:46][O:47][CH2:48][CH2:49]2)[CH2:32][CH2:33][O:34][CH2:35][CH2:36]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 67426575Bis-(3-morpholin-4-yl-propyl)-amine trihydrochlorideHCID 866428094-(3-Chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide

Product 1

HCID 866428572-(5-{[Bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amideYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.455 g (1.13 mmole) of 4-(3-chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.2b), 0.860 g (2.26 mmole) of bis-(3-morpholin-4-yl-propyl)-amine trihydrochloride and 50 mL of dichloromethane was stirred for 20 minutes, then 0.479 g 2.26 mmole) of sodium triacetoxy borohydride was added. The mixture was stirred for 4 days, then quenched by the addition of 50 mL of saturated sodium bicarbonate solution. The mixture was extracted three times with 50 mL of dichloromethane. The combined dichloromethane layers were washed with 50 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with dichloromethane-methanol (90:10) to give 0.210 g of 2-(5-{[bis-(3-morpholin-4-yl-propyl)-amino]-methyl}-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (VI.49a).

Workup

  1. stirringThe mixture was stirred for 4 days
  2. customquenched by the addition of 50 mL of saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted three times with 50 mL of dichloromethane
  4. washThe combined dichloromethane layers were washed with 50 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography
  9. washeluting with dichloromethane-methanol (90:10)

Sources & evidence

ORD record
ord-9906947a465e40a391931693e953828f
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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