1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → Tert-butyl 3-(3-(2-(5-(3,4-dimethylphenyl)pyrimidin-2-ylcarbamoyl)-4-(piperidin-1-yl)phenylcarbamoyl)benzylthio)propanoate

HRID 926792Notes

Reaction equation

HRID 926792 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][S:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.[NH2:33][C:34]1[CH:56]=[CH:55][C:54]([N:57]2[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]2)=[CH:53][C:35]=1[C:36]([NH:38][C:39]1[N:44]=[CH:43][C:42]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[C:47]([CH3:52])[CH:46]=2)=[CH:41][N:40]=1)=[O:37]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:52][C:47]1[CH:46]=[C:45]([C:42]2[CH:41]=[N:40][C:39]([NH:38][C:36]([C:35]3[CH:53]=[C:54]([N:57]4[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]4)[CH:55]=[CH:56][C:34]=3[NH:33][C:14]([C:13]3[CH:12]=[C:11]([CH:19]=[CH:18][CH:17]=3)[CH2:10][S:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:20])=[O:16])=[O:37])=[N:44][CH:43]=2)[CH:50]=[CH:49][C:48]=1[CH3:51]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665867133-((3-Tert-butoxy-3-oxopropylthio)methyl)benzoic acidHCID 665869432-amino-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-5-(piperidin-1-yl)benzamide

Product 1

HCID 66586925Tert-butyl 3-(3-(2-(5-(3,4-dimethylphenyl)pyrimidin-2-ylcarbamoyl)-4-(piperidin-1-yl)phenylcarbamoyl)benzylthio)propanoateYield 200%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

In a round bottom flask was placed a solution of 3-((3-tert-butoxy-3-oxopropylthio)methyl)benzoic acid (88.6 mg, 0.30 mmol, 1.20 equiv) in dichloromethane (15 mL), EDC.HCl (143.2 mg, 0.75 mmol, 3.00 equiv), 4-dimethylaminopyridine (152.1 mg, 1.24 mmol, 5.00 equiv), and 2-amino-N-(5-(3,4-dimethylphenyl)pyrimidin-2-yl)-5-(piperidin-1-yl)benzamide (100 mg, 0.25 mmol, 1.00 equiv). The resulting solution was stirred overnight at 25° C. in an oil bath. The resulting solution was diluted with 50 mL of dichloromethane. The resulting mixture was washed with 1×20 mL of diluted hydrochloric acid and 2×30 mL of brine. The mixture was dried over sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 340 mg of crude product as a brown syrup.

Workup

  1. customIn a round bottom flask was placed
  2. washThe resulting mixture was washed with 1×20 mL of diluted hydrochloric acid and 2×30 mL of brine
  3. dry with materialThe mixture was dried over sodium sulfate
  4. filtrationThe solids were filtered out
  5. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-5152bcb0b3f54fc69c9e2acc96fb2b93
Source dataset
uspto-grants-2016_03
Patent number
US09289429B2

Reaction notes

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